In Review: Amberjack Chelsea Boots

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“You’ve got the perfect face… to be a professional boot model!
– My wife, as she helped me take these photos
(Good help is hard to find)

Until recently, finding Chelseas that managed to successfully combine sharp style, supportive comfort, and strong value was a huge pain in the ass annoyingly difficult.

A lot of the elements that distinguish a boot as being well-made (like good-year welted construction and using high-quality boot material) also tend to make them heavy and uncomfortable, at least at first. 

As a result, even some of the best Chelsea boots require a long period of break-in time as the boot (oh-so-slowly) molds to the shape of your foot. 

And for guys who want both comfort and style, there’s another problem: traditionally, the most comfortable Chelseas have been the ones that put support way ahead of aesthetics. 

Old-school work boot brands like Blundstone and Wolverine have been making durable Chelseas that provide all-day comfort for years. 

But with chunky soles, rounded toes, and large profiles, they’re designed to keep you comfortable on a job site, not help you look sharp during business meetings, first dates, or formal occasions, all of which tend to require dressier looks.  

Enter Amberjack 

Into this fray enters Amberjack, a shoe brand that purports to solve this problem by focusing on style and support in equal measure. 

Two pairs of brown Amberjack Chelsea boots on display

After launching in 2020 with a dress shoe that combined a full-grain leather upper with sneaker-like features in the sole, they applied a similar formula to Chelseas in 2022. 

Their Chelsea boots have the sort of sleek toe shape usually reserved for uncomfortable dress shoes, but Amberjack claims they provide “surprisingly sweet comfort” thanks to midsoles and outsoles designed with proprietary support features. 

So, are the comfort and quality as high as they claim? Or is this yet another example of a brand making cheap boots that look great, but fail to hold up upon inspection? 

Read on to learn the full results of my Amberjack boots review and find out if their value matches their marketing claims. 

Key Takeaways ↓

I’ve owned a leather pair of Amberjack Chelseas for two years and a suede pair for about three months now, and overall I’m pretty impressed.

My full thoughts are below, but here’s a quick summary of the pros and cons:

What I Like About Amberjack’s Chelseas:

  • Sharp style: The Almond toe shape is classic and versatile, and the outsole is thinner than a lot of comparably comfortable sneaker boots.
  • High level of comfort: They were comfy right out of the box, with no break-in period required.
  • Quality materials: The leather is soft and supple, and the suede has a rich color and great texture.
  • Resilient construction: They’ve held up quite well after two years of wearing the hell out of ’em.
  • Fair price: They’re priced in the middle of the pack when compared to their competitors, but provide a lot of value for the money.

What I Don’t Like About ‘Em:

  • Unique seam: They have a seam that runs from the collar down to the sole, and I’m not sure how I feel about it.
  • No pull tab: This makes them look a little sleeker, but also a bit harder to pull on.
  • Cement construction: The boot has held up quite well, but it’s not welted, which may be a dealbreaker for some purists.

Amberjack Chelsea Boots Review 

Can comfort and style really co-exist?
An Irreverent Gent Investigation

Review Methodology & Disclosure

Amberjack provided Irreverent Gent with two pairs of Chelseas for editorial review, and I based my assessment on my personal experience with both. 

The first was a pair of leather Chelseas that they provided back in the spring of 2022, which I’ve been wearing regularly ever since. 

The other was a suede pair provided in the fall of 2023, which I’ve been wearing on and off throughout the winter months. 

I’ve practiced proper boot care exactly zero times over the past two years (not in the interest of thorough testing, just out of sheer laziness), which is probably worth taking into consideration.

Pair 1
(tested over 2 years)

Amberjack Chelseas in brown leather

Pair 2
(tested over 3 months)

Amberjack Chelseas in brown suede

This is a hands-on review based on my personal experience wearing both boots, and comparing them both to other boots in my collection and other popular models on the market.

Check out our product review and roundup policy here to learn more about how we rate and review products.

OK, preamble over. Let’s break down some boots, shall we?


(the shoe company, not the fish)

Amberjack logo

It’s worth taking a minute to discuss Amberjack as a company, because it has quite a bit more heft behind it than most direct-to-consumer startups. 

(If you’d prefer to skip this part and get straight to my assessment of the Amberjack boots themselves, click here to jump down to the review.)

Some Serious Shoe Credentials 

Amberjack was co-founded in 2020 by CEO John Peters, a former business consultant, with support from his business partner James Seuss, the former CEO of Cole Haan, and their friend Jake Rudin, a Senior Manager at Adidas. 

Their original idea was that, while technology and tastes were both evolving rapidly, dress shoes (mostly) weren’t. 

They liked the idea of combining athletic technology like memory foam with the style and full grain leather usually reserved for traditional dress shoes. 

“From a business standpoint, we aimed to offer a higher quality alternative to what brands like Cole Haan were doing”

– Amberjack CEO John Peters

And since one of their founders came from Cole Haan, they were obviously aware that there was demand for a hybrid shoe within the larger men’s shoe market—but they thought they could do it better. 

“From a business standpoint, we aimed to offer a higher quality alternative to what brands like Cole Haan were doing,” Peters told an interviewer in May of 2023. “We wanted to position ourselves at a higher price point and deliver superior quality, style, and material science.” 

To achieve that superiority, they turned to John Kraljevich, a shoe designer with decades of experience creating footwear for brands like Allen Edmonds, Coach and Rag & Bone. 

Committing to the higher price point that inevitably comes with high-quality products also meant creating their own proprietary materials, and streamlining the supply chain by partnering with some of the best tanneries in the world. 

Amberjack’s suede is sourced from top tanneries in Northern Italy; they’re a little more coy about where their leather comes from, but Bespoke Unit previously reported that they use a tannery in Monterrey, Mexico. 

Sleeker Than Most Hybrids 

Unlike the hybrids offered by brands like Wolf & Shepherd or Cole Haan, which have super chunky soles, Amberjack’s first offering, The Original, looked like a standard pair of leather shoes, making it easier to pull off at the office or on formal occasions. 

But despite the sleeker profile, the Amberjack Original uses heat-activated arch support and the company’s aforementioned proprietary outsole, so it provides just as much comfort as its thicker, more sneaker-looking competitors. 

We actually named The Original one of the most comfortable dress shoes on the market, so when Amberjack’s Chelseas hit the market I was curious to see how their approach would translate to a pair of boots. 

So without any further adieu, let’s take a look at Amberjack’s Chelsea boots and see how they stack up in terms of style, support, quality and value. 

Style & Aesthetics 

My First Impressions Right Outta The Box 

Two pairs of Amberjack Chelseas

I knew I’d have to wear the boots for a while to really test out the comfort features (on which more below), but I could tell pretty much as soon as I opened the box that these are stylish boots. 

The pictures on the Amberjack website make the Chelseas look very sleek, almost like they’d be too narrow if you have a wide foot. 

But in person they present with a little more heft, and strike a nice balance between sharp and rugged, which is more or less exactly what I’m going for come boot season. 

They might be a little tight if you have really wide feet, but for the vast majority of guys I think they’d work fine. 

Almond Toe Box 

One of the first things I noticed about Amberjack’s Chelseas, which I alluded to above, is the toe shape. 

While they’re not quite as sleek as my favorite Oxfords, they still have a nice almond-toe shape that’s classic, masculine and stylish, which helps them look a little more sophisticated than most Chelseas without feeling too “dressy.” 

Close up showing the toe box of the Amberjack Chelseas

(As an aside, I should point out that I tried the chestnut color in leather and “grizzly” brown version in suede. But I think the black boot would look significantly more formal, especially if you opt for the all-black model, rather than the one with a contrasting white midsole.) 

Narrow Collar  

You can kind of get a sense of the toe shape just by looking at the website, but one thing I didn’t realize until I got them in hand was how narrow the opening is at the top. 

I have a number of other Chelseas, including a casual pair with chunky lug soles that I bought at Marshall’s years ago (and whose brand name I don’t even remember), and a cheap-but-sleek pair of Bruno Marcs that’s specifically meant to be worn as dress boots.

Image comparing the opening of Amberjack's Chelseas to other brands

What’s interesting about the Amberjacks is that the collar – the opening at the top of the boot, where your foot slides in – is significantly more narrow than either pair, which helps them maintain a sleek profile. 

And even more impressively, the collar on my leather pair, which I’ve owned for two years and worn literally hundreds of times, is just as tight today as the one on my suede pair, which is only a few months old.

Close up showing two Amberjack boots from above, comparing their collars

That’s a great perk from a style perspective because it means that the boot has no trouble maintaining its shape, even after years of wear. 

But it arguably says even more about the construction, because it takes pretty high-quality leather to maintain its shape that well, not to mention the right balance between sturdy leather pieces and stretchy elastic panels.

Sleek Outsole 

In addition to the toe shape, another element that really helps distinguish Amberjack’s Chelseas from other comfy competitors is the outsole. 

Close up of the Amberjack Chelsea sole

I’m a fan of both Wolf & Shepherd and Cole Haan and own various models from both brands, but both have leaned heavily into the hybrid look, resulting in a distinctly more casual boot style. 

By contrast, Amberjack provides a lot of the same comfort (which, again, I’ll elaborate on below) while maintaining a sleeker sole, which gives it a more sophisticated and even formal style. 

It also makes them more versatile, since you can wear the Amberjacks in casual settings (where they’d give you a smarter, sharper look than chunky Cole Haans), or in more formal settings, like a business-casual office or even a semi-formal event

Unique (Weird? Less stylish? More stylish??) Seam 

There’s one thing about the look of Amberjack’s Chelseas that I’m (at best) on the fence about: 

They have a seam that runs from the collar of the boot, down the vamp and into the sole. 

Close up of the Amberjack Chelsea showing a seam running down the boot

It’s a unique look that I haven’t seen on many other boots, and to be honest I really have no idea how I feel about it. 

On the one hand it looks kind of cool, and helps distinguish them as a new style of boot that stands apart from a traditional, standard pair of Chelsea boots. 

But I honestly can’t decide whether or not that distinction is a good thing. A plain boot with no lines or seams would certainly be more classic, and arguably more sophisticated—but, I don’t know what points would really support that argument, other than the fact that unadorned boots are simply more common.

On a boot whose looks are otherwise unimpeachable, the seam is kind of a funny addition, and one I still haven’t fully wrapped my head around. 

Total Score for Style:

Style Pros and Cons:

Comfort & Support 

The three big comfort features that Amberjack promotes are the heat-activated arch support in the midsole, their dual-density outsole, and the soft sheepskin lining throughout, so let’s take a look at all three. 

The Midsole is Exceptional 👌

The outsole uses the proprietary material that Amberjack invented, but as someone who’s flat-footed, the arch support is probably the bigger draw for me, and I have to say I was quite impressed 

Like Amberjack’s other shoes, the Chelseas come with a removable insole that provides a lot of support right out of the gate. 

Close up of the Amberjack insole

Amberjack claims that it also molds nicely to your foot as your body heats it up over time, but after wearing them for a long time, I’m not sure how much molding has actually taken place. 

The suede Chelseas that I’ve only had for a few months feel just as comfortable as the leather ones that I’ve been wearing for years, which on the one hand is a testament to their comfort right out of the box, but also suggests that the footbed doesn’t change all that much over time.

With that said, Amberjack’s other claim about their midsoles has definitely proven true. Their website notes that their insole is “like memory foam but more durable, so it’ll stay supportive way longer.” 

This has definitely been borne out. As mentioned, the pair that I’ve owned for two years and worn hundreds of times feels just as comfy as the new pair, which is a testament to the insole’s ability to maintain its shape and support after a ton of wear. 

Two Amberjack insoles side by side
The older one has clearly (and embarrassingly) gotten quite a bit dirtier, but it’s maintained its shape and still provides the same level of support

These are probably the most comfortable Chelseas I’ve ever owned, and the insole is arguably the single biggest reason why. 

The Outsole is… Well, Fine, I Guess?

While the benefits of the insole are undeniable, the benefits of the custom TPU outsole are a little harder to pin down. 

Again, I have flat feet, so an insole that’s made with long-lasting arch support is going to do most of the heavy lifting in terms of comfort and support for me. 

But the outsole has also been helpful, especially when I first got the boots. I had a newborn baby at the time and we were still being very cautious about COVID, and doing some outside visits with friends and family. 

Close up of the Amberjack Chelsea outsole

That meant a lot of time spent standing on concrete in driveways or playgrounds, and the outsoles held up quite well. 

If I had popped the Amberjack insoles out of the boots and put them into another pair with a different outsole I suspect that I would have felt a lot of the same support, but it’s hard to say for sure. 

The Interior Lining is Pretty Luxurious 

The third factor has less to do with support, but quite a bit to do with comfort. 

The sheepskin lining is as soft as advertised, and another area where Amberjack’s claims prove accurate. 

I have other leather boots that feel stiff and almost painful when you first put them on, and require a long break-in period to really loosen up. 

By contrast, these were luxury-feeling boots right out of the box, which is ironic, because some of the stiffest and least comfortable boots I own come from luxury brands that boast about their incredible quality and hand-crafted techniques. 

So the fact that these were soft right from the jump was much appreciated, and a bit surprising given the price point and the quality of the leather (which I’ll expand on below). 

Total Score for Comfort:

Comfort Pros and Cons:

Quality & Craftsmanship 

As mentioned above, I got my first pair of Amberjack Chelseas back in 2022, and I’ve been wearing the hell out of ‘em for years. 

As a middle-aged dad who has to battle just to get his kids out the door each day, a sharp pair of Chelseas that I can slip on quickly while strapping kids into car seats is kind of a Godsend, so these have gotten a lot of use.

In fact, I wore them when we took the kids to the mall to meet Santa this year, as you can see below. 

Family photo showing Dave Bowden wearing Amberjack Chelseas
I briefly (briefly—I can’t stress that enough) considered cropping my family out of this pic to put even more emphasis on the boots, but couldn’t bring myself to do it

After years of use, I’ve been really impressed with how well Amberjack’s Chelseas have held up, and pleasantly surprised by both the quality of the leather and the durability of the construction. 

Luxe Leather

As I mentioned above, Amberjack puts a lot of emphasis on the high quality of its leather, and boasts about working with “the best tanneries in the world.” 

Screenshot from Amberjack website
Amberjack is not shy about bragging about mentioning its leather quality

However, they don’t actually mention the names of these tanneries or reveal where they’re located, which made me a little skeptical before trying the boots out for myself. 

But after two years of wearing the leather Chelseas everywhere, I’m happy to report that their leather is quite good quality. 

Cheap quality leather will often feel stiff and plasticky, and even crack after being folded or creased. 

But Amberjack’s leather is supple and flexible, and has proven remarkably resilient, even after plenty of exposure to direct sunlight and multiple foot races with my two-year-old in the park (which I dominated). 

Close up showing quality of Amberjack leather
Amberjack’s leather is quite soft and supple, which is particularly impressive after two years of heavy wear

I’ve only been wearing the suede pair for a few months so far, but they were fall and winter months, when the weather conditions were wet and messy. 

So far the weather-resistant suede has lived up to its billing and been quite resilient so far, maintaining both its texture and color after a number of nasty days. 

I’ll have to wear them for a few more months (and in a few different seasons) before I can deliver a final verdict, but so far all signs point to a similar level of longevity and quality. 

The other thing that’s impressed me with both the leather and suede is how well it’s held up despite a lack of proper care on my part. 

I used to be pretty militant about shining and polishing my shoes, but nowadays it’s never the first, second or even tenth most important thing on my to-do list. 

But the Chelseas have performed quite well despite my total and utter negligence, making them a good boot for guys who are too busy (or too apathetic) to spend much time on boot care. 


Another thing that made me a little skeptical when looking at the Chelseas online was the fact that Amberjack never mentions how the upper is attached to the sole. 

Many of the best men’s dress shoes and boots tend to be Goodyear welted, but hybrid boots like this almost never use that type of construction because it makes them a lot heavier. 

While Amberjack is mum on the subject, the same Bespoke Unit article I mentioned above reports that Amberjack’s shoes all seem to be cement-constructed, which makes sense. 

After two years of wearing the Chelseas frequently, I haven’t had any issues with Amberjack’s construction

Using a special adhesive cement to essentially glue the leather upper to the sole is a much lighter-weight alternative to welting, but the risk is that poorly glued or cemented shoes can start to come apart over time. 

This is a particular hobby horse for me because when I was younger the only shoes I could afford were from cheap mall brands like Aldo, which I’d quickly wear into the ground. 

On more than one occasion, the upper started to peel right off the sole, as if my foot were a God damn banana,  just waiting to emerge.  

This is where I’m glad that I waited so long to write my review, because after two years of wearing the Chelseas frequently I haven’t had any issues with Amberjack’s construction, despite the lack of welting. 

Again, Amberjack doesn’t mention this on their website so I’m not sure what their method is or what kind of cement they use, but after some pretty thorough testing I feel confident in saying that whatever it is, it works. 

Total Score for Quality:

Quality Pros and Cons:

Price & Value 

Amberjack Price Comparisons

BootPriceSneaker-like Comfort?Chelsea?
Amberjack Chelseas$195
Cole Haan ØriginalGrand Ultra Chelsea$95
Hush Puppies Detroit Chelsea$99
Johnston & Murphy Upton Chelsea$165
Wolf & Shepherd Crossover™ Hiker WTZ$409
Allen Edmonds Liverpool Chelsea$495
Amberjack Chelseas$195
Cole Haan ØriginalGrand Ultra Chelsea$95
Hush Puppies Detroit Chelsea$99
Johnston & Murphy Upton Chelsea$165
Wolf & Shepherd Crossover Hiker WTZ$409
Allen Edmonds Liverpool Chelsea$495

Amberjack Price Analysis 

Price illustration

Amberjack’s Chelseas cost about $200, which puts them in the middle of the pack when compared to some of their closest competitors. 

They’re twice as expensive as the ØriginalGrand Chelseas from Cole Haan and the Detroit Chelsea from Hush Puppies, which as noted above, is by design on Amberjack’s part. 

They’re closer in price to the Johnston & Murphy Upton Chelsea, which has good reviews on both Johnston & Murphy’s site and Amazon

But it also has a sneaker-like heel that makes it look less sophisticated, and only comes in brown leather, both of which make it less sleek than the Amberjack. 

Beyond that it gets tricky to find good comparisons for the Amberjacks because there aren’t many other boots that are really apples-to-apples. 

Allen Edmonds makes a great Chelsea that’s arguably more stylish and better constructed than the Amberjack. But it’s also not a hybrid and costs more than twice as much.  

On the other side of the comfort spectrum, Wolf & Shepherd’s Crossover Hiker is comfy as hell, but a totally different type of shoe, and also twice as expensive. 

Based on both my personal experience wearing Amberjack’s Chelseas and a comparison to other boots on the market, I would say Amberjack is well priced in terms of value-for-money. 

You can find some boots that are just as comfortable and well-made, and others that are just as stylish (or even more so), but none that offer the same combination of style and comfort in one package. 

Total Score for Price & Value:

Conclusion & Final Thoughts

Collage of images showing Amberjack chelseas

After two years spent wearing the hell out of one pair and a few months spent testing another, I’m pretty impressed by Amberjack’s Chelseas

They manage to do something that should be easy, but is surprisingly (and annoyingly) rare in the world of men’s boots: 

Achieve equally high levels of style, comfort, and quality. 

The almond toe shape is both sophisticated and versatile, the “fancy foam” footbed is as comfortable as advertised, and after two years of pretty regular wear, they’ve proven to be quite resilient, despite the lightweight construction. 

I probably wouldn’t recommend them for super formal occasions like weddings, where a proper pair of dress boots would be more appropriate for pairing with a suit. 

Nor are they the best bet if you’re looking for casual sh*t kickers that can get you through winter, in which case something like a lug-tread Blundstone would probably work best. 

But if you want a stylish and comfortable pair of everyday boots that falls right in the middle of that spectrum, these are a great choice at a fair price. 

Overall Score for Amberjack Chelseas: 4.3 / 5

The Recap ↓

Overall Score for Amberjack’s Chelseas

Dave Bowden

Style & Aesthetics: 4/5
Comfort & Support: 4.5/5
Quality & Craftsmanship: 4.7/5
Price & Value: 4/5


I’ve owned a leather pair of Amberjack Chelseas for two years and a suede pair for about three months now, and overall I’m pretty impressed. They manage to do something that should be easy, but is surprisingly (and annoyingly) rare in the world of men’s boots: Achieve equally high levels of style, comfort, and quality.



FAQ illustration

More Resources ↓
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About Dave Bowden

Dave Bowden

Founder, Irreverent Gent
Author, Man in Command and Stop Doubting, Start Dating
Writer, Really Wordy Author Bios

Dave Bowden is a style blogger, menswear expert and best-selling author (in Canada—but still!) whose advice on how to look good and live well has been featured in New York Magazine, The Wall Street Journal, Men's Health and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and two amazing sons, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well (don't worry—it's less creepy than it sounds!), or email him at [email protected] if you want to get in touch.

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