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Updated September 2024
✅ 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
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True to size
on Amberjack.com
on Amberjack.com
Free shipping, free returns, and two year warranty
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.
Runs small
on Nisolo.com
60 day return policy, no warranty
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
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
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
Runs large
on Blundstone.com
30 day return policy, one year warranty
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.
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Me and my shoes
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Me and my shoes
True to size
on JohnstonandMurphy.com
30 day return policy, one year warranty
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.
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Wolf & Shepherd dress shoe side profile
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Wolf & Shepherd Top shot
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.
| Brand | Comfort | Style | Versatillity | Quality and Durability | Value | Fit | Overall |
|---|---|---|---|---|---|---|---|
Amberjack | 5 | 4.5 | 5 | 5 | 4.5 | 4.5 | 4.8 |
| Allen Edmonds | 4.5 | 4.5 | 4.5 | 5 | 3.5 | 4 | 4.3 |
| Wolf & Shepherd | 5 | 4.5 | 4 | 4.5 | 3 | 4.5 | 4.3 |
| Johnston & Muephy | 4.5 | 4 | 4 | 4 | 4.5 | 4 | 4.2 |
| ECCO | 4.5 | 3 | 3.5 | 4.5 | 3.5 | 4 | 3.8 |
| Cole Haan | 3.5 | 3.5 | 4 | 3 | 4 | 3.5 | 3.6 |
| Rockport | 3.5 | 3 | 3.5 | 3.5 | 3.5 | 3.5 | 3.4 |
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