The Best Men's Chelsea Boots 2025
updated JAN 2025

I own a LOT of boots. I've walked hundreds of miles in them, I've interviewed experts and spent hundreds of hours researching. Here you'll benefit from my obsession and my deep dive on Chelsea's! Here are my results:

5,000+
reviews analyzed
100+
hours wearing Chelsea's
30+
Chelsea boots considered
7
Chelsea boots purchased
winner #1 out of 7
Best Everyday Chelsea Boot
Amberjack
4.8/5
Amberjack
4.8/5.0
featured in
Sizing: Standard and Wide (runs true to size)
Colors:
Material: Full-Grain Leather, Italian Suede, Nubuck
View Boots ($199)
Visit Amberjack.shop
featured in
Sizing: Standard and Wide (runs true to size)
Colors:
Material: Full-Grain Leather, Italian Suede, Nubuck
Pros
Sleek, classic, and modern design
Beautiful tanned leathers
Most comfortable Chelsea I tried
Perfect for daily, all day wear
Great for work & casual settings
Handmade in Portgual
Sleek, classic, and modern design
Thick insole for added support
Comfortable sheepskin interior lining
Strong midsole and great arch support
Wide toe box to prevent cramping
Flexible leather avoids chafing
Athletic technology built into sole
Cozy fit around ankle
Cons
Can't purchase on Amazon
Limited availability in-person
Too many marketing emails
Overall
Amberjack, scored high marks across all the factors I cared about. These are some really good looking Chelsea's and the comfort is unbelievable. They've got a narrow, elastic collar which looks and feels great. Additionally, the streamlined design looks fantastic without sacrificing comfort due to the flexibility of the leather. My favorite part is the combo of the sheepskin interior lining with the thick insole.

More Details

The factors that mattered to me when testing
Aesthetic
Looks great today & over time
Comfort
Can wear it all day, comfortably
Durability
Built for daily or regular wear
Quality
Premium material & craftsmanship
Versatility
Suitable for casual + formal
Value
Great bang for your buck
How I chose these Chelseas
There are literally hundreds of Chelsea Boots out there so identifying which boot is going to be a great addition to my wardrobe is challenging. Here's how I narrowed it down:

Consulted footwear experts - I reviewed top publications from industry experts to see recommendations.

Rated high on comfort - I only chose boots that scored high on comfort from customer reviews.

Strong customer reviews - I eliminated any brand that scored lower than 4.5 stars for their customer reviews.

Brown and multiple color options - I excluded shoes that did not have a brown option as its one of the most versatile colors. I also excluded shoes that did not have multiple color options.

No luxury boots - I wanted them to be accessible so I eliminated anything over $500.
Having fun styling and wearing my Chelsea boots.
How I ranked each boot
Aesthetic test: I styled them with different looks
Comfort test: I rigorously evaluated comfort
Durability research: I put miles on each boot
Quality test: Deep dive on boot materials
Versatility test: How well they did across looks
Value: Summed scores & compared with price
How I Tested Comfort
There is more to get right comfort-wise with a Chelsea Boot. Here is what I look at:
Insole: I use calipers to measure the thickness of the insole. Thicker insoles provide more comfort and alleviate foot pain.
Outsole: Is it leather or rubber? What kind (Butyl treated, TPU, EVA, Crepe)? This affects the feel, look, and durability.
Midsole: This connects the insole to the outsole. It's the source of cushioning and shock absorption.
Wear test: I use the shoes and see how they feel from extended wear.
Interior lining: Some shoes feel like you're putting on socks, others chafe. Here we look at the material, thickness, breathability, and cushioning.
Collar: This is what rests against your ankle. I look at fit, padding, elasticity, stitching, and if it has a pull tab/how good is the pull tab.
Amberjack had the thickest insole by far!
My pick for the best Chelsea Boot
winner #1 out of 7
Best Everyday Chelsea Boot
Amberjack
4.8/5
featured in
Amberjack
4.8/5.0
featured in
Width: Standard & Wide (true to size)
Colors:
Material: Full-Grain Leather, Italian Suede, Nubuck
Things to note: Free shipping & returns, 2 year warranty
View Boots ($199)
Visit Amberjack.shop
Width: Standard & Wide (true to size)
Colors:
Material: Leather, Italian Suede, Nubuck
Things to note: Free shipping & returns, 2 year warranty
Pros
Sleek, classic, and modern design
Beautiful tanned leathers
Most comfortable Chelsea I tried
Perfect for daily, all day wear
Sleek, classic, and modern design
Premium A-Grain Leather
Unique, highly durable stitching
Available in 11 colors
Thick insole for added support
Comfortable sheepskin interior lining
Strong midsole and great arch support
Wide toe box to prevent cramping
Flexible leather avoid chafing
Athletic technology built into sole
Cons
Can't purchase on Amazon
Limited availability in-person
Too many marketing emails
No pull tabs (some guys prefer this)
Overall
Amberjack, scored high marks across all the factors I cared about. These are some really good looking Chelsea's and the comfort is unbelievable. They've got a narrow, elastic color which looks and feels great. Additionally, the streamlined design looks fantastic without sactificing comfort due to the flexibility of the leather. My favorite part is the combo of the sheepskin interior lining with the thick insole.
Works for conference room and for dinner after work!
👍 What I love ️
(1) Very comfortable: They market comfort and they really do nail it. They've been exceptionally thoughtful about all the details. Specifically, the interior sheepskin lining, the thick insoles, they use a proprietary TPU midsole/outsole which incorporates athletic and hiking technology. You really feel the support without the ugly blockiness some outsoles have that use similar tech. Last, but not least is the flexibility of the leather. They've managed to create an upper that does not rub or chafe. You'll feel great all day in these shoes.

(2) Aesthetic: I'm a fan of their Chestnut color personally. Deep brown pairs well with pretty much anything. Additionally, I love the narrow collar because it looks great with jeans or under a suit. I also am a big fan of the classic Chelsea look with the streamlined design (I prefer this over wider/chunkier Chelseas). They have a unique stitching pattern on the front. I wasn't sure I'd like it, but I was a fan in person. It's fairly understated and I think adds to the look. It's also one of the secrets behind that flexible leather upper.

(3) Premium materials and craftsmanship: The use of A-Grade leather in their boot as well as sheepskin lining on the interior. The quality of the stitching is high and it's difficult to nail the flexibility of that leather upper. The construction is cemented (some guys may prefer a goodyear welt), but they have direct relationships with all of their suppliers. The manufacturer is a high quality Portuguese house that's grown with Amberjack over the years and has a reputation high quality shoes. Additionally, they've invested into a high quality outsole/insole that really sets them a part. You're getting a durable, well made shoe. Their two year warrant is also fairly uncommon and shows they back their quality claims.

(4) Value for Money: There are a lot of boots that look great, use great material, and charge a fair price. What puts Amerjack over the top on value is they do all of that while also being the most comfortable shoe on the market hands down. I've found boots that index on comfort/durability to be a bit more expensive. Amberjack doing all that they do at $190 is impressive.
👎 What could be better
(1) Limited Availability: The inability to purchase on Amazon or try on in-store may be a drawback for some consumers who prefer these shopping methods.

(2) Aggressive Marketing: The frequency of marketing emails could be off-putting to those who prefer less inbox clutter.
Looks great in a suit, jeans, pants and very comfortable.
Full-grain leather: Amberjack leather uses the highest quality and most durable type of leather. It is made from the top layer of the animal hide, which contains the strongest and most tightly packed fibers.
TPU: Amberjack proprietary sole is one of only two brands using a TPU sole. This provide an optimal combination of comfort and durability. It ensures the shoe remains comfortable and functional over time.
runner up #2 of 7 products
Nisolo
4.5/5
Nisolo
4.5/5.0
Width: Standard (true to size)
Colors:
Material: Leather
Things to mention: No warranty
View Boots ($268)
Visit Nisolo.com
Width: Standard (true to size)
Colors:
Material: Leather
Things to mention: No warranty
Pros
Sleep, modern, and classic design
Beautiful, limited color range
Cushioned memory insole for support
Low stacked heel for reduced strain
Soft, breathable leather
Slip proof rubber lug sole
Pull tab
B-Corp sustainably made product
High quality, durable construction
Water resistant leather upper
Cons
Most expensive boot on this list
Limited color options
Requires a little breaking in (leather)
Not enough support on midsole/outsole
Interior lining provides ok comfort
Overall
Nisolo makes a beautiful Chelsea boot. If you're okay paying the $270 tag you're getting a well made, sustainably crafted product with the sleek, modern and classic look of a Chelsea boot. The standout is I think all of their color options are beautiful. These boots come in Brown, Mahogany, Black, and Tobacco. They lose some points on comfort and price, but you can't go wrong with this Chelsea.
The pull tabs can interfere with pants
👍 What I love ️
️(1) Excellent color range: The color range is fantastic. It's limited, but the options they have are stunning.

(2) Modern, sleek aesthetic: 
This is a great looking boot that can work well with any outfit. If you need to dress something up or dress it down, you can sport this with any outfit.

(3) Certified B-Corp:
This is becoming more important to people every year, but Nisolo's commitment to a net zero carbon footprint is impressive and difficult.

(4) High quality leather and construction -
This boot will handle itself well and can take daily wear thanks to the rubber lug, slip resistant sole. The uppers are leather working group certified as well as water resistant.
👎 What could be better
(1) Expensive pricing: The high cost can be prohibitive for some buyers, and it will be expensive for many. That said, many find the quality justifies the price. I personally think there are buys out there of better value, but it is a great option.

(2) Requires break-in period:
The brand claims there is no break in period required but I personally found the uppers to be a bit stiff on first wear. They should gradually soften and mold to your foot over time, but it will take some wearing.

(3) Limited color range and materials:
While the colors are beautiful the number of options limited. For anyone looking to expand their Chelsea boot collection this may present a challenge.

(4) Interior lining is okay:
I expected more from Nisolo on comfort to be honest given how much they market it on their site. I think they do pretty well on the leather and the insole, but I wanted a bit more on the lining. It's just not as comfortable as that sheepskin lining on the Amberjacks and for the $270 I'd expect to love how they feel on the inside.
A good looking and well made shoe.
#3 of 7 products
Florsheim
4.3/5
Florsheim
4.3/5.0
Width: D-medium, 3E-wide
Colors:
Material: Leather, Suedetec, Rubber
Things to mention: 30 day return policy
View Boots ($140)
Visit Florsheim.com
Width: D-medium, 3E-wide
Colors:
Material: Leather, Suedetec, Rubber
Things to mention: 30 day return policy
Pros
Best looking color of any Chelsea I tried
Classic Chelsea look
Soft Suedetec lining
Fully cusioned, moldable EVA sole
Excellent value
Wide fit available
No heel slip, snug fit
Ready to wear out of the box
Pull tab
Cons
Not versatile (i.e. more dressy)
Chunky, wider collar
Leather upper is stiff
Not enough midsole/outsole support
Reviews report durability issues
Overall
The Florsheim Rucci Plain Toe Gore Chelsea stands out with its striking aesthetics and classic design. It offers a blend of comfort features and style, making it an attractive option for those seeking a more dressy Chelsea boot. While it excels in certain areas, there are some trade-offs in versatility and support that potential buyers should consider.
Beautiful Mahogany color on this Florsheim boot.
👍 What I love ️
(1) Aesthetic Appeal: Boasting the best-looking color of any Chelsea I tried, this boot makes a strong visual impression.

(2) Classic Design: The boot stays true to the classic Chelsea look, perfect for those who appreciate traditional styling.

(3) Comfort Features: Soft Suedetec lining and a fully cushioned, moldable EVA sole provide a comfortable wearing experience.

(4) Value for Money: Excellent value proposition, offering a good balance of features and style at its price point.
👎 What could be better
(1) Versatility: The more dressy style limits its versatility for casual wear.

(2) Boot Profile:
The chunky design and wider collar may not appeal to those preferring a sleeker silhouette.

(3) Leather Quality:
The stiff leather upper might require a break-in period for optimal comfort.

(4) Support:
Not enough midsole/outsole support, which could be an issue for all-day wear or people needing more arch support.

(5) Durability Concerns:
Some reviews report durability issues, which might affect the boot's long-term value.
#4 of 7 products
Thursday Boot
4.2/5
Thursday Boot
4.2/5.0
Width: Standard, Wide
Colors:
Material: Leather, Elastic, Cork
Things to mention: 30 day return policy
View Boots ($190)
Visit ThursdayBoots.com
Width: Standard, Wide
Colors:
Material: Leather, Elastic, Cork
Things to mention: 30 day return policy
Pros
Sleek classic design
Full grain LeFarc sourced leather
Soft cowhide interior lining
Goodyear welt construction
Thursday boot studded outsole
Flexible leather upper, four panels
Resoleable boot
Wide fit available
Comfortable shock absorbing insoles
Free shipping
Cons
Slightly loose fit
Underperformed on comfort
Reported issues with shape retention
Wider/chunkier collar
Support could be better
Overall
This Chelsea boot combines classic design with high-quality materials and construction techniques. It offers a blend of style and durability, with features that cater to both aesthetics and longevity. While it has some notable strengths in materials and craftsmanship, there are areas where comfort and fit could be improved.
Historic company, classic boot. Love my Thursday's.
👍 What I love ️
(1) Classic Aesthetics: The sleek classic design makes it a versatile choice for various outfits and occasions.

(2) Premium Materials:
Full grain LeFarc sourced leather and soft cowhide interior lining speak to the quality of materials used.

(3) Durable Construction:
Goodyear welt construction and a studded outsole (Thursday boot) contribute to the boot's longevity and performance.

(4) Longevity:
Being a resoleable boot adds to its long-term value and sustainability.
👎 What could be better
(1) Fit Issues: The slightly loose fit might affect the overall wearing experience and comfort for some users.

(2) Comfort Expectations:
Despite comfort features, the boot underperformed on comfort, suggesting room for improvement.

(3) Shape Retention:
Reported issues with shape retention could affect the boot's appearance over time.

(4) Boot Profile:
The wider/chunkier collar may not appeal to those seeking a sleeker silhouette.

(5) Support:
The support could be better, which might be a concern for those needing more arch support or planning for extended wear.
#5 of 7 products
Blundstone
3.8/5
Blundstone
3.8/5.0
Width: True to size, Relaxed fit
Colors:
Material: Leather, Elastic, Rubber
Things to mention: 30 day returns, Free shipping
View Boots ($200)
Visit Blundstone.com
Width: True to size, Relaxed fit
Colors:
Material: Leather, Elastic, Rubber
Things to mention: 30 day returns, Free shipping
Pros
Rugged, outdoor look
Premium waterproof leather
Leather lined interior
Comfort EVA insole
Polyurethane midsole for comfort
XRD Tech in heel for shock absorption
Comes with an extra set of footbeds
Water resistant design
Pull tabs
Cons
Not suitable for more formal wear
High price point
Large collar, tough to fit on ankle
Requires break in period
Not as snug of a fit on heel
Not as comfortable as I'd lke
Overall
The Blundstone Chelsea boot is designed for the outdoors, offering a rugged look combined with waterproof functionality. It's built with comfort and durability in mind, featuring multiple layers of technology to enhance the wearer's experience. However, its outdoor-focused design comes with some trade-offs in versatility and initial comfort.
Rugged. Looks great with some jeans.
👍 What I love ️
(1) Outdoor Functionality: Rugged look and water-resistant design make it perfect for outdoor activities.

(2) Premium Materials:
Waterproof leather and leather-lined interior speak to the quality of construction.

(3) Comfort Technology:
Comfort EVA insole, polyurethane midsole, and XRD Tech in the heel provide multiple layers of comfort and shock absorption.

(4) Extras:
Comes with an additional set of footbeds for customized fit.

(5) Convenience:
Pull tabs make it easy to put on and take off.
👎 What could be better
(1) Versatility: Not suitable for more formal wear, limiting its use to casual and outdoor settings.

(2) Price:
High price point may not fit everyone's budget.

(3) Fit Issues:
Large collar can be tough to fit on the ankle, and the heel fit is not as snug as desired.

(4) Break-in Period:
Requires time to break in, which might be inconvenient for some users.

(5) Comfort Expectations:
Despite the comfort features, it's not as comfortable as I'd like.
Thick soles, water resistant boots.
#6 of 7 products
Johnston Murphy
3.6/5
Johnston Murphy
3.6/5.0
Width: True to size
Colors:
Material: Leather, Elastic, Rubber
Things to mention: 30 day return policy, 1 year warranty
View Boots ($268)
Visit JohnstonMurphy.com
Width: True to size
Colors:
Material: Leather, Elastic, Rubber
Things to mention: 30 day return policy, 1 year warranty
Pros
Extremely lightweight shoe
Full-grain leather
Proprietary TRUFOAM sole for comfort
Double stiched leather welt
Memory-foam cushioned insole
Available in various colors
Recognizable brand name
Cons
Don't love stitching around outsole
Outsole is too casual
Stitching around collar is not classic
Durability issues reported
Leather upper is stiff
Overall
The Johnston & Murphy Chelsea boot stands out for its lightweight design and comfort features. It combines classic style with modern comfort technology, making it a versatile choice for everyday wear. However, some design elements and potential durability issues may give pause to traditional Chelsea boot enthusiasts.
I don't love the block sole, but it works with jeans.
👍 What I love ️
(1) Lightweight Design: Extremely lightweight shoe, reducing foot fatigue during extended wear.

(2) Quality Materials:
Full-grain leather upper ensures durability and a premium look.

(3) Comfort Features:
Proprietary TRUFOAM sole and memory-foam cushioned insole provide excellent comfort.

(4) Construction:
Double stitched leather welt adds to the boot's durability.

(5) Brand Recognition:
Recognizable brand name associated with quality footwear.
👎 What could be better
(1) Aesthetic Details: Stitching around the outsole and collar deviates from classic Chelsea boot design.

(2) Formality: Outsole is too casual for more formal occasions, limiting versatility.

(3) Durability: Some reported durability issues raise concerns about long-term value.

(4) Break-in Period: Leather upper is stiff initially, requiring a break-in period.
#7 of 7 products
Huckberry
3.4/5
Huckberry
3.4/5.0
Width: True to size
Colors:
Material: Suede, Rubber, Leather
Things to mention: 30 day return policy
View Boots ($250)
Visit Huckberry.com
Width: True to size
Colors:
Material: Suede, Rubber, Leather
Things to mention: 30 day return policy
Pros
Premium European leather
Soft interior leather lining
Natural Crepe rubber sole
Chrome tanning, easier to break in
Accessible to wider feet
Roomy fit
Cons
Gets dirty easily
Not suitable for more formal wear
Higher price point
Not as comfortable as advertised
Overall
The Huckberry Chelsea boot offers a blend of premium materials and comfort-focused design. It caters well to those with wider feet and prioritizes a roomy fit. While it excels in material quality and accessibility, it falls short in some areas of comfort and versatility.
👍 What I love ️
(1) Premium Materials: High-quality European leather and soft interior leather lining provide a luxurious feel.

(2) Luxury Design:
Natural Crepe rubber sole looks awesome.

(3) Easy Break-in:
Chrome tanning process makes the leather easier to break in.

(4) Inclusive Sizing:
Accessible to wider feet with a roomy fit.
👎 What could be better
(1) Maintenance: Gets dirty easily, which might require more frequent cleaning.

(2) Versatility: Not suitable for more formal wear, limiting its use to casual settings.

(3) Price: Higher price point may not be accessible to all budgets.

(4) Comfort Expectations: Despite comfort-focused design, it's not as comfortable as advertised.
My dress shoe scoring system
Brand
Comfort
Style
Versatility
Quality + Durability
Value
Price
Overall
Amberjack
5
4.5
5
5
4.5
$189
4.8
Nisolo
4.5
4.5
4.5
5
3.5
$350
4.3
Florsheim
5
4.5
4
4
3
$395
4.2
Thursday Boot
4.5
4
4
4
4.5
$155
4.2
Blundstone
4.5
5
3.5
4.5
3.5
$150
3.8
Johnston Murphy
3.5
3.5
4
3.5
4
$200
3.6
Huckberry
3.5
3
3.5
3.5
3.5
$89
3.4
Scrollable horizontally
Why I chose Amberjack
Amberjack Chelsea boots were the standout choice for me - they do a great job of scoring high marks across comfort, style, and versatility. These boots are great for daily wear. You get all-day comfort without sacrificing a sleek, modern aesthetic. The materials are high quality and the thoughtful design features, such as the supportive insole and flexible leather, ensure you'll get a really comfortable boot that lasts. The durability and versatility of Amberjack boots make them a worthwhile investment for those seeking a go-to Chelsea boot that can transition seamlessly from casual to more formal settings.
Thanks for reading!
By Alvaro Anspach - Chelsea Boot Obsessed
I passionate about boots and obsessed with Chelseas. I spent tons of hours testing Chelsea boots to find the best.
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The Best Chelsea Boots For Men in 2024
updated SEP 2024
I'm obsessed with boots

I own a LOT of boots. I've walked hundreds of miles in them, I've interviewed experts, and spent hundreds of hours researching. Here you'll benefit from my obsession and my deep dive on Chelsea's!

5,000+
reviews analyzed
100+
hours wearing Chelsea's
30+
Chelsea boots considered
7
Chelsea boots purchased
winner #1 out of 7
Best for Style & Comfort
Amberjack
4.8/5.0
Amberjack
4.8/5.0
featured in
Sizing: Standard and Wide (runs true to size)
Colors:
Material: Full-Grain Leather, Italian Suede, Nubuck
View Boots ($199)
Visit Amberjack.shop
featured in
Sizing: Standard and Wide
Colors:
Material: Full-Grain Leather, Italian Suede, Nubuck
Pros
Sleek, classic, and modern design
Beautiful tanned leathers
Most comfortable Chelsea boot I tried
Perfect for everyday, all day wear
Great for work & casual settings
Handmade in Portgual
Thick insole for added support
Comfortable sheepskin interior lining
Strong midsole and great arch support
Wide toe box to prevent cramping
Flexible leather avoids chafing
Athletic technology built into sole
Cozy fit around ankle
Cons
Can't purchase on Amazon
Limited availability in-person
Too many marketing emails
Overall
Amberjack, scored high marks across all the factors I cared about. These are some really good looking Chelsea's and the comfort is unbelievable. They've got a narrow, elastic collar which looks and feels great. Additionally, the streamlined design looks sleek without sacrificing comfort due to the flexibility of the leather. My favorite part is the combo of the sheepskin interior lining with the thick insole.

More Details

What I look for in a Chelsea Boot
All my chelsea boots stacked up!
There are literally hundreds of Chelsea Boots out there so identifying which boot is going to be a great addition to my wardrobe is challenging. For me any boot needs to meet these criteria to be considered:
The Factors I Tested
Aesthetic
Looks great today & over time
Comfort
Can wear it all day, comfortably
Durability
Built for daily or regular wear
Value
Great bang for your buck
Versatility
Suitable for casual + formal
Quality
Premium material & craftsmanship
Having fun styling and wearing my Chelsea boots.
How I Tested Comfort
There is more to get right comfort-wise with a Chelsea Boot. Here is what I look at:
Insole: I use calipers to measure the thickness of the insole. Thicker insoles provide more comfort and alleviate foot pain.
Outsole: Is it leather or rubber? What kind (Butyl treated, TPU, EVA, Crepe)? This affects the feel, look, and durability.
Midsole: This connects the insole to the outsole. It's the source of cushioning and shock absorption.
Wear test: I use the shoes and see how they feel from extended wear.
Interior lining: Some shoes feel like you're putting on socks, others chafe. Here we look at the material, thickness, breathability, and cushioning.
Collar: This is what rests against your ankle. I look at fit, padding, elasticity, stitching, and if it has a pull tab/how good is the pull tab.
Amberjack had the thickets insole by far!
My pick for the best Chelsea Boot
winner #1 out of 7
Best For Style & Comfort
Amberjack
4.8/5.0
featured in
Amberjack
4.8/5.0
featured in
Width: Standard & Wide (true to size)
Colors:
Material: Full-Grain Leather, Italian Suede, Nubuck
Things to note: Free shipping & returns, 2 year warranty
View Boots ($199)
Visit Amberjack.shop
Width: Standard & Wide (true to size)
Colors:
Material: Leather, Italian Suede, Nubuck
Things to note: Free shipping & returns, 2 year warranty
Pros
Most comfortable brand I tried
Perfect for daily, all day wear
Sleek, classic, and modern design
Premium A-Grain Leather
Unique, highly durable stitching
Available in 11 colors
Thick insole for added support
Comfortable sheepskin interior lining
Strong midsole and great arch support
Wide toe box to prevent cramping
Flexible leather avoid chafing
Athletic technology built into sole
Cons
Can't purchase on Amazon
Limited availability in-person
Too many marketing emails
No pull tabs (some guys prefer this)
Overall
Amberjack, scored high marks across all the factors I cared about. These are some really good looking Chelsea's and the comfort is unbelievable. They've got a narrow, elastic collar which looks and feels great. Additionally, the streamlined design looks sleek without sacrificing comfort due to the flexibility of the leather. My favorite part is the combo of the sheepskin interior lining with the thick insole.
Works for conference room and for dinner after work!
👍 What I love ️
(1) Very comfortable: They market comfort and they really do nail it. They've been exceptionally thoughtful about all the details. Specifically, the interior sheepskin lining, the thick insoles, they use a proprietary TPU midsole/outsole which incorporates athletic and hiking technology. You really feel the support without the ugly blockiness some outsoles have that use similar tech. Last, but not least is the flexibility of the leather. They've managed to create an upper that does not rub or chafe. You'll feel great all day in these shoes.

(2) Aesthetic: I'm a fan of their Chestnut color personally. Deep brown pairs well with pretty much anything. Additionally, I love the narrow collar because it looks great with jeans or under a suit. I also am a big fan of the classic Chelsea look with the streamlined design (I prefer this over wider/chunkier Chelseas). They have a unique stitching pattern on the front. I wasn't sure I'd like it, but I was a fan in person. It's fairly understated and I think adds to the look. It's also one of the secrets behind that flexible leather upper.

(3) Premium materials and craftsmanship: The use of A-Grade leather in their boot as well as sheepskin lining on the interior. The quality of the stitching is high and it's difficult to nail the flexibility of that leather upper. The construction is cemented (some guys may prefer a goodyear welt), but they have direct relationships with all of their suppliers. The manufacturer is a high quality Portuguese house that's grown with Amberjack over the years and has a reputation for high quality shoes. Additionally, they've invested into a high quality outsole/insole that really sets them a part. You're getting a durable, well made shoe. Their two year warrant is also fairly uncommon and shows they back their quality claims.

(4) Value for Money: There are a lot of boots that look great, use great material, and charge a fair price. What puts Amberjack over the top on value is they do all of that while also being the most comfortable shoe on the market hands down. I've found boots that index on comfort/durability to be a bit more expensive. Amberjack doing all that they do at $199 is impressive.
👎 What could be better
(1) Limited Availability: The inability to purchase on Amazon or try on in-store may be a drawback for some consumers who prefer these shopping methods.

(2) Aggressive Marketing: The frequency of marketing emails could be off-putting to those who prefer less inbox clutter.
Looks great in a suit, jeans, pants and very comfortable.
Full-grain leather: Amberjack leather uses the highest quality and most durable type of leather. It is made from the top layer of the animal hide, which contains the strongest and most tightly packed fibers.
TPU: Amberjack proprietary sole is one of only two brands using a TPU sole. This provide an optimal combination of comfort and durability. It ensures the shoe remains comfortable and functional over time.
runner up #2 of 7 products
Nisolo
4.5/5.0
Nisolo
4.5/5.0
Width: Standard (true to size)
Colors:
Material: Leather
Things to mention: No warranty
View Boots ($268)
Visit Nisolo.com
Width: Standard (true to size)
Colors:
Material: Leather
Things to mention: No warranty
Pros
Sleep, modern, and classic design
Beautiful, limited color range
Cushioned memory insole for support
Low stacked heel for reduced strain
Soft, breathable leather
Slip proof rubber lug sole
Pull tab
B-Corp sustainably made product
High quality, durable construction
Water resistant leather upper
Cons
Most expensive boot on this list
Limited color options
Requires a little breaking in (leather)
Not enough support on midsole/outsole
Interior lining provides ok comfort
Overall
Nisolo makes a beautiful Chelsea boot. If you're okay paying the $270 tag you're getting a well made, sustainably crafted product with the sleek, modern and classic look of a Chelsea boot. The standout is I think all of their color options are beautiful. These boots come in Brown, Mahogany, Black, and Tobacco. They lose some points on comfort and price, but you can't go wrong with this Chelsea.
The pull tabs can interfere with pants
👍 What I love ️
️(1) Excellent color range: The color range is fantastic. It's limited, but the options they have are stunning.

(2) Modern, sleek aesthetic: 
This is a great looking boot that can work well with any outfit. If you need to dress something up or dress it down, you can sport this with any outfit.

(3) Certified B-Corp:
This is becoming more important to people every year, but Nisolo's commitment to a net zero carbon footprint is impressive and difficult.

(4) High quality leather and construction -
This boot will handle itself well and can take daily wear thanks to the rubber lug, slip resistant sole. The uppers are leather working group certified as well as water resistant.
👎 What could be better
(1) Expensive pricing: The high cost can be prohibitive for some buyers, and it will be expensive for many. That said, many find the quality justifies the price. I personally think there are buys out there of better value, but it is a great option.

(2) Requires break-in period:
The brand claims there is no break in period required but I personally found the uppers to be a bit stiff on first wear. They should gradually soften and mold to your foot over time, but it will take some wearing.

(3) Limited color range and materials:
While the colors are beautiful the number of options limited. For anyone looking to expand their Chelsea boot collection this may present a challenge.

(4) Interior lining is okay:
I expected more from Nisolo on comfort to be honest given how much they market it on their site. I think they do pretty well on the leather and the insole, but I wanted a bit more on the lining. It's just not as comfortable as that sheepskin lining on the Amberjacks and for the $270 I'd expect to love how they feel on the inside.
A good looking and well made shoe.
#3 of 7 products
Florsheim
4.3/5.0
Florsheim
4.3/5.0
Width: D-medium, 3E-wide
Colors:
Material: Leather, Suedetec, Rubber
Things to mention: 30 day return policy
View Boots ($140)
Visit Florsheim.com
Width: D-medium, 3E-wide
Colors:
Material: Leather, Suedetec, Rubber
Things to mention: 30 day return policy
Pros
Best looking color of any Chelsea I tried
Classic Chelsea look
Soft Suedetec lining
Fully cusioned, moldable EVA sole
Excellent value
Wide fit available
No heel slip, snug fit
Ready to wear out of the box
Pull tab
Cons
Not versatile (i.e. more dressy)
Chunky, wider collar
Leather upper is stiff
Not enough midsole/outsole support
Reviews report durability issues
Overall
The Florsheim Rucci Plain Toe Gore Chelsea stands out with its striking aesthetics and classic design. It offers a blend of comfort features and style, making it an attractive option for those seeking a more dressy Chelsea boot. While it excels in certain areas, there are some trade-offs in durability, comfort, and versatility that made it lose some points. Overall this is a great Chelsea if you're on a tighter budget.
Beautiful Mahogany color on this Florsheim boot.
👍 What I love ️
(1) Aesthetic Appeal: Boasting the best-looking color of any Chelsea I tried, this boot makes a strong visual impression.

(2) Classic Design: The boot stays true to the classic Chelsea look, perfect for those who appreciate traditional styling.

(3) Comfort Features: Soft Suedetec lining and a fully cushioned, moldable EVA sole provide a comfortable wearing experience.

(4) Value for Money: Excellent value proposition, offering a good balance of features and style at its price point.
👎 What could be better
(1) Versatility: The more dressy style limits its versatility for casual wear.

(2) Boot Profile:
The chunky design and wider collar may not appeal to those preferring a sleeker silhouette.

(3) Leather Quality:
The stiff leather upper might require a break-in period for optimal comfort.

(4) Support:
Not enough midsole/outsole support, which could be an issue for all-day wear or people needing more arch support.

(5) Durability Concerns:
Some reviews report durability issues, which might affect the boot's long-term value.
#4 of 7 products
Thursday Boot
4.2/5.0
Thursday Boot
4.2/5.0
Width: Standard, Wide
Colors:
Material: Leather, Elastic, Cork
Things to mention: 30 day return policy
View Boots ($190)
Visit ThursdayBoots.com
Width: Standard, Wide
Colors:
Material: Leather, Elastic, Cork
Things to mention: 30 day return policy
Pros
Sleek classic design
Full grain LeFarc sourced leather
Soft cowhide interior lining
Goodyear welt construction
Thursday boot studded outsole
Flexible leather upper, four panels
Resoleable boot
Wide fit available
Comfortable shock absorbing insoles
Free shipping
Cons
Slightly loose fit
Underperformed on comfort
Reported issues with shape retention
Wider/chunkier collar
Support could be better
Overall
This Chelsea boot is perfect for anyone that wants a brand with history and tradition. Thursday, combines classic design with high-quality materials and construction techniques. It's a great looking, well made shoe. They lose some points on comfort and I think the collar is too chunky to pair well with a more modern suit, but this is another great boot for someone who values tradition.
Historic company, classic boot. Love my Thursday's.
👍 What I love ️
(1) Classic Aesthetics: The sleek classic design makes it a versatile choice for various outfits and occasions.

(2) Premium Materials:
Full grain LeFarc sourced leather and soft cowhide interior lining speak to the quality of materials used.

(3) Durable Construction:
Goodyear welt construction and a studded outsole (Thursday boot) contribute to the boot's longevity and performance.

(4) Longevity:
Being a resoleable boot adds to its long-term value and sustainability.
👎 What could be better
(1) Fit Issues: The slightly loose fit might affect the overall wearing experience and comfort for some users.

(2) Comfort Expectations:
Despite comfort features, the boot underperformed on comfort, suggesting room for improvement.

(3) Shape Retention:
Reported issues with shape retention could affect the boot's appearance over time.

(4) Boot Profile:
The wider/chunkier collar may not appeal to those seeking a sleeker silhouette.

(5) Support:
The support could be better, which might be a concern for those needing more arch support or planning for extended wear.
#5 of 7 products
Blundstone
3.8/5.0
Blundstone
3.8/5.0
Width: True to size, Relaxed fit
Colors:
Material: Leather, Elastic, Rubber
Things to mention: 30 day returns, Free shipping
View Boots ($200)
Visit Blundstone.com
Width: True to size, Relaxed fit
Colors:
Material: Leather, Elastic, Rubber
Things to mention: 30 day returns, Free shipping
Pros
Rugged, outdoor look
Premium waterproof leather
Leather lined interior
Comfort EVA insole
Polyurethane midsole for comfort
XRD Tech in heel for shock absorption
Comes with an extra set of footbeds
Water resistant design
Pull tabs
Cons
Not suitable for more formal wear
High price point
Large collar, tough to fit on ankle
Requires break in period
Not as snug of a fit on heel
Not as comfortable as I'd lke
Overall
The Blundstone Chelsea might feel out of place on this list, but it is the perfect workman's boot. This boot is designed for the outdoors, offering a rugged look combined with waterproof functionality. It's built with comfort and durability in mind, featuring multiple layers of tech. This boot is perfect for anyone that is likely to get their shoes dirty and wants something that can hold up and still look good.
Rugged. Looks great with some jeans.
👍 What I love ️
(1) Outdoor Functionality: Rugged look and water-resistant design make it perfect for outdoor activities.

(2) Premium Materials:
Waterproof leather and leather-lined interior speak to the quality of construction.

(3) Comfort Technology:
Comfort EVA insole, polyurethane midsole, and XRD Tech in the heel provide multiple layers of comfort and shock absorption.

(4) Extras:
Comes with an additional set of footbeds for customized fit.

(5) Convenience:
Pull tabs make it easy to put on and take off.
👎 What could be better
(1) Versatility: Not suitable for more formal wear, limiting its use to casual and outdoor settings.

(2) Price:
High price point may not fit everyone's budget.

(3) Fit Issues:
Large collar can be tough to fit on the ankle, and the heel fit is not as snug as desired.

(4) Break-in Period:
Requires time to break in, which might be inconvenient for some users.

(5) Comfort Expectations:
Despite the comfort features, it's not as comfortable as I'd like.
Thick soles, water resistant boots.
#6 of 7 products
Johnston Murphy
3.6/5.0
Johnston Murphy
3.6/5.0
Width: True to size
Colors:
Material: Leather, Elastic, Rubber
Things to mention: 30 day return policy, 1 year warranty
View Boots ($268)
Visit JohnstonMurphy.com
Width: True to size
Colors:
Material: Leather, Elastic, Rubber
Things to mention: 30 day return policy, 1 year warranty
Pros
Extremely lightweight shoe
Full-grain leather
Proprietary TRUFOAM sole for comfort
Double stiched leather welt
Memory-foam cushioned insole
Available in various colors
Recognizable brand name
Cons
Don't love stitching around outsole
Outsole is too casual
Stitching around collar is not classic
Durability issues reported
Leather upper is stiff
Overall
The Johnston & Murphy Chelsea boot stands out for its lightweight design. It combines classic style with modern comfort technology, making it a versatile choice for everyday wear. However, I'm not a huge fan of the stark weight rubber sole and they lost some points on durability, quality, and value. The look is also not quite classic enough so it won't work on all occasions.
I don't love the block sole, but it works with jeans.
👍 What I love ️
(1) Lightweight Design: Extremely lightweight shoe, reducing foot fatigue during extended wear.

(2) Quality Materials:
Full-grain leather upper ensures durability and a premium look.

(3) Comfort Features:
Proprietary TRUFOAM sole and memory-foam cushioned insole provide excellent comfort.

(4) Construction:
Double stitched leather welt adds to the boot's durability.

(5) Brand Recognition:
Recognizable brand name associated with quality footwear.
(1) Aesthetic Details: Stitching around the outsole and collar deviates from classic Chelsea boot design.

(2) Formality: Outsole is too casual for more formal occasions, limiting versatility.

(3) Durability: Some reported durability issues raise concerns about long-term value.

(4) Break-in Period: Leather upper is stiff initially, requiring a break-in period.
👎 What could be better
#7 of 7 products
Huckberry
3.4/5.0
Huckberry
3.4/5.0
Width: True to size
Colors:
Material: Suede, Rubber, Leather
Things to mention: 30 day return policy
View Boots ($250)
Visit Huckberry.com
Width: True to size
Colors:
Material: Suede, Rubber, Leather
Things to mention: 30 day return policy
Pros
Premium European leather
Soft interior leather lining
Natural Crepe rubber sole
Chrome tanning, easier to break in
Accessible to wider feet
Roomy fit
Cons
Gets dirty easily
Not suitable for more formal wear
Higher price point
Not as comfortable as advertised
Overall
The Huckberry Chelsea is a great looking mountain boot. Its made of premium materials and is marketed as comfort-focused. Personally I think this boot is great for a winter getaway to the mountains but lacks in versatility, durability, and comfort so its not my first choice for a daily Chelsea boot.
👍 What I love ️
(1) Premium Materials: High-quality European leather and soft interior leather lining provide a luxurious feel.

(2) Luxury Design:
Natural Crepe rubber sole looks awesome.

(3) Easy Break-in:
Chrome tanning process makes the leather easier to break in.

(4) Inclusive Sizing:
Accessible to wider feet with a roomy fit.
👎 What could be better
(1) Maintenance: Gets dirty easily, which might require more frequent cleaning.

(2) Versatility: Not suitable for more formal wear, limiting its use to casual settings.

(3) Price: Higher price point may not be accessible to all budgets.

(4) Comfort Expectations: Despite comfort-focused design, it's not as comfortable as advertised.
My dress shoe scoring system
Brand
Comfort
Style
Versatility
Quality + Durability
Value
Price
Overall
Amberjack
5
4.5
5
5
4.5
$199
4.8
Nisolo
4.5
4.5
4.5
5
3.5
$268
4.5
Florsheim
5
4.5
4
4
3
$140
4.3
Thursday Boot
4.5
4
4
4
4.5
$190
4.2
Blundstone
4.5
5
3.5
4.5
3.5
$200
3.8
Johnston Murphy
3.5
3.5
4
3.5
4
$169
3.6
Huckberry
3.5
3
3.5
3.5
3.5
$250
3.4
Scrollable horizontally
Why I chose Amberjack
Amberjack Chelsea boots were the standout choice for me - they do a great job of scoring high marks across comfort, style, and versatility. These boots are great for daily wear. You get all-day comfort without sacrificing a sleek, modern aesthetic. The materials are high quality and the thoughtful design features, such as the supportive insole and flexible leather, ensure you'll get a really comfortable boot that lasts. The durability and versatility of Amberjack boots make them a worthwhile investment for those seeking a go-to Chelsea boot that can transition seamlessly from casual to more formal settings.
Thanks for reading!
By Alvaro Anspach - Chelsea Boot Obsessed
I'm passionate about boots and obsessed with Chelseas. I spent tons of hours testing Chelsea boots to find the best.
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The Best Chelsea Boots for Men 2024

Updated September 2024

Want the recap? I wanted to find the most comfortable dress shoes I could wear to work. After speaking to footwear experts and personally testing 20 dress shoe brands I chose the top 8 most comfortable brands. Here are my results:
The Best Men's Dress Shoes 2024

Updated March 2024

Want the TLDR? I tested 10 dress shoe brands to find the most stylish and comfortable option. Here's the winner.

What I look for in a Chelsea

There are literally hundreds of Chelsea Boots out there so identifying which boot is going to be a great addition to my wardrobe is challenging. For me any boot needs to meet three criteria to be considered:

1. Comfortable - You don't have to sacrifice comfort for style. In fact, I'd argue that high quality boots prioritize comfort as part of their design.

2. Aesthetic - Chelsea boots should elevate any look. I want boots that look great with a variety of outfits and in a ton of different settings.

3. Durability -
I live in New York so I put miles on my shoes. If I'm going to invest a couple hundred dollars into a shoe I want it to last.

4. Value - I care about value. I'm flexible on price, but I want my money's worth. If we're going to pay up it needs to reflect in the quality and craftsmanship of the boot.
With that in mind I only reviewed boots that:

1. Rated high on comfort
2. Cost less than $500
3. Available for purchase online
4. History of strong reviews

The factors I evaluated in the Chelsea Boots I tested

✅ Comfort - Can wear it all day, comfortably
✅ Aesthetic -
Looks great today & over time
✅ Versatility -
Suitable for casual + formal
✅ Durability -
Built for daily or regular wear
✅ Quality - Premium material & craftsmanship
✅ Value -
Great bang for your buck

Walking in each shoe on my way to work.

How I evaluated comfort & tested my Chelsea's

Evaluating comfort and durability

  • Insole: I bought calipers to properly measure the thickness of each shoes insole. Thicker insoles provide more comfort and help to alleviate foot pain.
  • Outsole: Is it leather or rubber? What kind (Butyl treated, TPU, EVA, Crepe? These choices affect the feel, look, and durability of the boot.
  • Midsole: This connects the insole to the outsole. It's the primary source of cushioning and shock absorption. It also seriously affects the look of the shoe. Here we pay attention to material, construction method, stack height, heel to toe drop and more.
  • Interior lining: Some shoes feel like you're putting on socks, others chafe. Here we look at the material, thickness, breathability, and cushioning.
  • Collar: This is what rests against your ankle. I look at fit, padding, elasticity, stitching, and if it has a pull tab/how good is the pull tab.
  • Wear test: I use the shoes and see how they feel from extended wear.

How I tested all of the shoes

  • Wear test: I wore all of the Chelsea several times, testing for comfort and feel.
  • Caliper test: I measured the insoles of all the boots to evaluate the thickness and comfort of the sole.
  • Styling test: I wore the boots with different outfits (casual, classic, formal) to see the aesthetic and versatility.
  • Material & construction analysis: I researched and inspect the construction method, leather, and materials.
  • Value score: I gave each boot a value score. With everything you're getting, does the price reflect the value?
  • Overall rank: I summed up all the scores for each boot across every category to get an overall rank.
Amberjack had the thickets insole by far!

The details about quality and durability that you need to know

There are four main components to quality and durability

1. Leather quality: In order of highest to lowest quality of leather you have 1. Full grain leather 2. Top grain leather and 3. Corrected grain leather. You want to look for shoes that have full grain leather as those are highest quality. They retain the full natural grain of the hide, including any imperfections, which contributes to its durability and unique character.

2. Material of the outsole (bottom of shoe): There are four types of soles you can look at 1. TPU 2. EVA 3. Rubber 4. Leather. The most comfortable shoes either use TPU, EVA, or Rubber. The most durable material is TPU. It's the material that is used in hiking, athletic shoes, and performance wear.

3. Construction method: Every shoe on this list is made using cement construction so they the comparisons are apple to apple. There are higher quality construction methods (i.e. goodyear welt or blake stitch) but they are less common in dress shoes designed for comfort.

4. Quality of internal components: Here we look at the quality of the insole/midsole, footbed material, stitching, shape and space of the toe box, and more.

My pick for the best Chelsea Boot

★ Winner ★

Amberjack

True to size

View Shoes ($189)

on Amberjack.com

View Shoes ($189)

on Amberjack.com

Check Price

Free shipping, free returns, and two year warranty

4.8/5

What I love

  • Most comfortable brand I tried

  • Beautiful and versatile Chestnut color

  • Sleek, classic, and modern design

  • Available in 9 different colors

  • Full grain leather or suede option

  • Thick insole for added support

  • Very comfortable sheepskin interior lining

  • Strong midsole and great arch support

  • Wider toe box to prevent cramping

  • Accommodates wide feet

  • Flexible leather avoids chafing

  • Athletic technology built into sole

  • Cozy fit around ankle

  • Extremely breathable material

  • Perfect for work & casual settings

  • Portuguese craftsmanship

  • Built for daily wear

What I don't like

  • Can't purchase on amazon

  • No pull tabs (some guys prefer this)

  • Limited availability in-person

  • Too many marketing emails

⭐ Overall rating ️

Amberjack, scored high marks across all the factors I cared about. These are some really good looking Chelsea's and the comfort is unbelievable. They've got a narrow, elastic color which looks and feels great. Additionally, the streamlined design looks fantastic without sactificing comfort due to the flexibility of the leather. My favorite part is the combo of the sheepskin interior lining with the thick insole. This shoe is very comfortable. The only downside (which to me is not a real downside) is the lack of a pull tab. I know some guys love that feature, but personally I think it can mess with the look especially if you're wearing a suit. These are easy enough to slip on without the tab. This is my favorite Chelsea and I can't recommend it enough.

👍 What I love ️

(1) Very comfortable: They market comfort and they really do nail it. They've been exceptionally thoughtful about all the details. Specifically, the interior sheepskin lining, the thick insoles, they use a proprietary TPU midsole/outsole which incorporates athletic and hiking technology. You really feel the support without the ugly blockiness some outsoles have that use similar tech. Last, but not least is the flexibility of the leather. They've managed to create an upper that does not rub or chafe. You'll feel great all day in these shoes.

(2) Aesthetic: I'm a fan of their Chestnut color personally. Deep brown pairs well with pretty much anything. Additionally, I love the narrow collar because it looks great with jeans or under a suit. I also am a big fan of the classic Chelsea look with the streamlined design (I prefer this over wider/chunkier Chelseas). They have a unique stitching pattern on the front. I wasn't sure I'd like it, but I was a fan in person. It's fairly understated and I think adds to the look. It's also one of the secrets behind that flexible leather upper.

(3) Premium materials and craftsmanship: The use of A-Grade leather in their boot as well as sheepskin lining on the interior. The quality of the stitching is high and it's difficult to nail the flexibility of that leather upper. The construction is cemented (some guys may prefer a goodyear welt), but they have direct relationships with all of their suppliers. The manufacturer is a high quality Portuguese house that's grown with Amberjack over the years and has a reputation high quality shoes. Additionally, they've invested into a high quality outsole/insole that really sets them a part. You're getting a durable, well made shoe. Their two year warrant is also fairly uncommon and shows they back their quality claims.

(4) Value for Money: There are a lot of boots that look great, use great material, and charge a fair price. What puts Amerjack over the top on value is they do all of that while also being the most comfortable shoe on the market hands down. I've found boots that index on comfort/durability to be a bit more expensive. Amberjack doing all that they do at $190 is impressive.

👎 What could be better

Limited Availability:The inability to purchase on Amazon or try on in-store may be a drawback for some consumers who prefer these shopping methods.

No pull tab: For anyone that values a pull tab these Chelsea's don't sport one. That said, they are easy to slip on and I think the look is cleaner in jeans or a suit pant.

Aggressive Marketing:The frequency of marketing emails could be off-putting to those who prefer less inbox clutter.

Opening the Amberjack box. Sleek!

Full-grain leather - Amberjack leather uses the highest quality and most durable type of leather. It is made from the top layer of the animal hide, which contains the strongest and most tightly packed fibers.

TPU - Amberjack proprietary sole is one of only two brands using a TPU sole. This provide an optimal combination of comfort and durability. It ensures the shoe remains comfortable and functional over time.

Look good, feel good.

Runner Up:
Nisolo

Runs small

View Shoes ($268)

on Nisolo.com

Check Price

60 day return policy, no warranty

4.5/5

What I love

  • Sleek, modern and classic design

  • Beautiful, limited color range

  • Cushioned memory insole for support

  • Low stacked heel for reduced strain

  • Soft, breathable leather

  • Slip proof rubber lug sole

  • Pull tab

  • B-Corp sustainably made product

  • High quality, durable construction

  • Water resistant leather upper

What I don't like

  • Most expensive boot on this list

  • Limited color options

  • Requires a little breaking in (leather uppers)

  • Not enough support on midsole/outsole

  • Interior leather lining provides okay comfort

⭐ Overall rating

Nisolo makes a beautiful Chelsea boot. If you're okay paying the $270 tag you're getting a well made, sustainably crafted product with the sleek, modern and classic look of a Chelsea boot. The standout is I think all of their color options are beautiful. These boots come in Brown, Mahogany, Black, and Tobacco. They lose some points on comfort and price, but you can't go wrong with this Chelsea.

👍 What I love ️

Excellent color range: The color range is fantastic. It's limited, but the options they have are stunning.

Modern, sleek aesthetic: This is a great looking boot that can work well with any outfit. If you need to dress something up or dress it down, you can sport this with any outfit.

Certified B-Corp: This is becoming more important to people every year, but Nisolo's commitment to a net zero carbon footprint is impressive and difficult.

High quality leather and construction - This boot will handle itself well and can take daily wear thanks to the rubber lug, slip resistant sole. The uppers are leather working group certified as well as water resistant.


👎 What could be better

Expensive pricing:
The high cost can be prohibitive for some buyers, and it will be expensive for many. That said, many find the quality justifies the price. I personally think there are buys out there of better value, but it is a great option.

Requires break-in period: The brand claims there is no break in period required but I personally found the uppers to be a bit stiff on first wear. They should gradually soften and mold to your foot over time, but it will take some wearing.

Limited color range and materials: While the colors are beautiful the number of options limited. For anyone looking to expand their Chelsea boot collection this may present a challenge.

Interior lining is okay: I expected more from Nisolo on comfort to be honest given how much they market it on their site. I think they do pretty well on the leather and the insole, but I wanted a bit more on the lining. It's just not as comfortable as that sheepskin lining on the Amberjacks and for the $270 I'd expect to love how they feel on the inside.

Clean look on the Allen Edmonds shoes

Top shot of the Allen Edmonds dress shoes

Thursday Boot

True to size

View Shoes ($190)

on Thursdayboot.com

Check Price

90 day return policy

4.4/5

What I love

  • Sleek classic design

  • Full grain LeFarc sourced leather

  • Soft cowhide interior lining

  • Goodyear welt construction

  • Thursday boot studded outsole

  • Flexible leather upper, four panels

  • Resoleable boot

  • Wide fit available

  • Multiple color options available

  • Comfortable shock absorbing insoles

  • Free shipping

What I don't like

  • Slightly loose fit

  • Underperformed on comfort

  • Reported issues with shape retention

  • Wider/chunkier collar

  • Support could be better

⭐ Overall rating ️

Johnston & Murphy is similar in many ways to the Cole Haan, but I thought the style of the Cole Haan edged it out. That said, for people that prefer a bolder stitching pattern and want a comfortable, versatile dress shoe with a sneaker-like look this is a great choice.

👍 What I love ️

Stylish and professional appearance:
The brand successfully balances modern trends with classic professionalism in their designs.

Comfortable fit: They generally run true to size and you can trust the sizing guides.

👎 What could be better

Requires break-in period: The shoes may need time to soften and conform to the foot. This means you're in for a bit of an uncomfortable experience right out of the gate.

Inconsistent quality: There can be noticeable differences in quality between their budget-friendly and premium lines. The shoe we reviewed that is their go-to daily shoe ranked lower on quality and durability to other brands due to the material and craftsmanship. We also saw quality issues reported more often in their reviews relative to other brands and even with the models we found in the store, scuff marks appeared easily on the soles.

Photo of front stitching, top shot, sligh peel

Florsheim

Runs large

View Shoes ($140)

on ColeHaan.com

Check Price

30 day return policy

4.0/5

What I love

  • Best looking color of any Chelsea I tried

  • Classic Chelsea look

  • Soft and comfortable Suedetec lining

  • Fully cushioned, moldable EVA insole

  • Excellent value

  • Wide fit available

  • No heel slip, snug fit

  • Ready to wear out of the box

  • Pull tab

What could be better

  • Not as versatile (i.e. more dressy)

  • Chunky, wider collar

  • Leather upper is a bit stiff

  • Not enough midsole/outsole support

  • Reviews reporting durability issues

⭐ Overall rating ️

Let me start by saying that Cole Haan creates a great shoe. It bridges the gap between the traditional dress shoes and modern comfort technology (i.e. hybrid shoes). They do this at a more accessible price point than brands like Allen Edmonds and Wolf & Shepherd. Their shoe is great for anyone that is looking for a comfortable dress shoe with a sportier look.

👍 What I love ️

Stylish and contemporary designs:
Cole Haan gives you a polished shoe that has more of a sneaker like/athletic appearance. If you want something that leans more casual these are a great option.

Comfortable cushioning: The ZeroGrand is very comfortable. They felt awesome to try on and were very lightweight.

Good value for money: I think the quality is lower than the Amberjacks, but its definitely much higher than some of the budget brands like Rockport/Clark's/etc. You won't have these shoes for life but you'll get decent wear out of them.

Lightweight construction:Their shoes often feel more like sneakers than traditional dress shoes, which keeps your foot feeling fresh.

Wide range of colors and styles: They have a ton of different options for colors.

👎 What could be better

Basic design: Not a lot of variation. Overall I felt that the design and aesthetic of this shoe was a little basic. Specifically the stitching around the sole and the stark contrast between the leather and the sole.

Some durability and concerns: May not hold up as well to frequent, heavy use compared to brands like Amberjack, Allen Edmonds, and Wolf & Shepherd. This was a consistent complaint found amongst reviews and you can tell when you're wearing the shoe.

Quality concerns: This is an affordable shoe (I'd say its in the middle on price) but I don't think the quality justifies the price. Specifically, I think the longevity on the shoe is lower and its less of an investment.

Cole Haan angle shot

Blundstone

Runs large

View Shoes ($200)

on Blundstone.com

Check Price

30 day return policy, one year warranty

3.8/5

What I love

  • Rugged, outdoor look

  • Premium waterproof leather

  • Leather lined interior

  • Comfort EVA insole

  • Polyurethane midsole for comfort

  • XRD® Tech in heel for shock absorption

  • Comes with an extra set of footbeds

  • Available in various colors and finishes

  • Water resistant design

  • Pull tabs

What I don't like

  • Not suitable for more formal wear

  • Higher price point

  • Large collar, tough to fit on ankle

  • Requires break in period

  • Not as snug of a fit on heel

⭐ Overall rating ️

ECCO has an insanely comfortable shoe. It's a close race between this and Amberjack for comfort. For someone who values comfort above all and wants to stay within a very tight budget this is a great option.

👍 What I love ️

Superior comfort and support: ECCO shoes are renowned for their out-of-the-box comfort, requiring little to no break-in period. Can confirm these feel like clouds on your feet.

High-quality materials: The brand uses premium leathers and innovative synthetic materials that contribute to both durability and comfort. They will last you a long time.

Great for all-day wear: The construction and materials make these shoes ideal for those who are on their feet for extended periods.

Excellent for walking and standing: The ergonomic design and cushioning provide great support for someone that is always on their feet.

Durable sole construction: ECCO's soles are built to last, often outlasting the uppers of the shoes.

👎 What could be better

Design is not as modern or stylish: I personally think these shoes are not very nice and I would not wear them at work. This is a highly functional shoe and does not pay as much attention to form in my opinion.

Me and my shoes

Me and my shoes

Johnston Murphy

True to size

View Shoes ($169)

on JohnstonandMurphy.com

Check Price

30 day return policy, one year warranty

3.6/5

What I love

  • Extremely lightweight shoe

  • Full-grain leather

  • Proprietary TRUFOAM™ sole for comfort

  • Double-stitched leather welt

  • Memory-foam cushioned insole

  • Available in various colors

What could be better

  • Don't love the stitching around outsole

  • Outsole is too casual for more formal wear

  • Stitching around collar is not classic

  • Durability issues reported

  • Leather upper is stiff

⭐ Overall rating ️

Wolf & Shepherd has designed a luxury shoe and priced it accordingly, but I think they miss the mark on style and versatility. This is a very comfortable shoe and the quality is pretty good, but in no way does it justify the $395 price tag in my opinion with the big blocky sole, the lack of versatility (looks like a traditional dress shoe), and the quality of the construction should be much higher given the price.

👍 What I love ️

Very comfortable: Wolf & Shepherd does a great job of making a comfortable dress shoe. You get great support from the TPU sole, the collar is snug, the insoles are great. It's really well done.

Quality materials: The leather is A-Grade, the sole is TPU, and they've invested in their insoles.

Classic design: Barring the blocky sole this looks like a class dress shoe and is a great fit for someone who wants something more traditional.

👎 What could be better

Not great value: I find the price for the offering to be completely off the mark. The quality should be higher and the style/design should be nicer given what they are charging.

Limited color options: They only have two color options for this shoe making the selection extremely limited.

Limited color options: They only have two color options for this shoe making the selection extremely limited.

Blocky sole: I am not a fan of the blocky sole. I think its extremely visible and draws too much attention.

Durability issues: I'm surprised at how many durability issues are reported given the price point of the shoe, but this was another negative mark for me.

Wolf & Shepherd dress shoe side profile

Wolf & Shepherd Top shot

Huckberry

True to size

View Shoes ($250)

on Huckberry.com

Check Price

30 day return policy

3.4/5

What I love

  • Premium European leather

  • Soft interior leather lining

  • Natural Crepe rubber sole

  • Chrome tanning, easier to break in

  • Accessible to wider feet

  • Roomy fit

What I don't love

  • Gets dirty easily

  • Not suitable for more formal wear

  • Higher price point

  • Not as comfortable as advertised

⭐ Overall rating ️

Rockport successfully combines the comfort of athletic shoes with the style of dress shoes, offering a good balance of functionality and affordability. They're particularly well-suited for those in business casual environments or who prioritize comfort in their dress shoes.

👍 What I love ️

Comfortable and durable: Rockport's use of athletic shoe technology results in shoes that are comfortable right out of the box and built to last.

Good value for money: The brand offers decent quality shoes at a more accessible price point than many competitors.

Lightweight designs: Many models feel significantly lighter than traditional dress shoes, reducing foot fatigue.

👎 What could be better

Fit is difficult to assess: Like some other brands, sizes can vary between different styles, making online purchases challenging.

Some designs may be too basic: While functional, I personally find Rockport's styles lack the sophistication of higher-end dress shoe brands.

May not be suitable for very formal occasions: The casual-leaning designs might not be appropriate for the most formal business or social events.

Durability issues: This brand was the most cited for durability issues with wear on the soles and stitching often reported.

My dress shoe scoring system

BrandComfortStyleVersatillityQuality and DurabilityValueFitOverall
Amberjack54.5554.54.54.8
Allen Edmonds4.54.54.553.544.3
Wolf & Shepherd54.544.534.54.3
Johnston & Muephy4.54444.544.2
ECCO4.533.54.53.543.8
Cole Haan3.53.54343.53.6
Rockport3.533.53.53.53.53.4
Brand
Comfort
Style
Versatillity
Quality + Durability
Value
Price
Overall

Amberjack
5
4.5
5
5
4.5
$189
4.8
Nisolo
4.5
4.5
4.5
5
3.5
$268
4.3
Thursday Boot
4
4
4
5
4.5
$190
4.2
Florsheim
4
4
4
4
5
$140
4.2
Blundstone
4
3
3.5
4.5
3.5
$200
3.8
Johnston Murphy
3.5
3
4
3.5
4
$169
3.6
Huckberry
3.5
4.5
3.5
4
3.5
$250
3.4
Brand
Comfort
Style
Versatillity
Quality
Value
Price
Overall
Amberjack
★Winner★

Amberjack
5
4.5
5
5
4.5
$189
4.8
Allen Edmonds
4.5
4.5
4.5
5
3.5
$350
4.3
Wolf & Shepherd
5
4.5
4
4.5
3
$395
4.3
Johnston & Murphy
4.5
4
4
4
4.5
$155
4.2
ECCO
4.5
5
3.5
4.5
3.5
$150
3.8
Cole Haan
3.5
3.5
4
3
4
$200
3.6
Rockport
3.5
3
3.5
3.5
3.5
$89
3.4

Why I chose Amberjack

If you're in the market for a new pair of dress shoes that will serve you well throughout 2024 and beyond, I highly recommend giving Amberjack a try.

Their combination of comfort, style, and quality is hard to beat, and they're suitable for a wide range of occasions from daily office wear to formal events.

Remember, the perfect dress shoe is one that not only looks good but feels good too. It should be an investment in your comfort, confidence, and professional appearance.

With Amberjack, you're getting all of that and more. Whether you're a busy professional like me, someone who's on their feet all day, or just someone who appreciates a great pair of shoes, Amberjack is worth considering. Your feet will thank you!