There aren’t many pieces of menswear as versatile, stylish and convenient as a good pair of Chelsea boots.

With elastic side panels that negate the need for (and time-consuming annoyance of) laces, Chelseas are the easiest type of ankle boots to slip on and off.

Plus they give you an undeniably classic look, and stem from a pretty bad-ass sartorial tradition that dates back to the Victorian era, and evokes the Beatles, the Rolling Stones and the swinging scene of ‘60s London.

Unfortunately, not all Chelseas are created equal—and many aren’t even created all that comfortably.

Case and point? When GQ did a roundup of the best men’s Chelsea boots, they ranked the Wyatt dress boot from Saint Laurent as their top overall pick.

Saint Laurent Wyatt Chelsea — GQ’s favorite Chelsea boot *looks* sleek and sexy, but likely feels stiff and uncomfortable (plus it costs a f*cking fortune)

And, look, it’s a pretty handsome pair of boots, and that black leather sure looks buttery soft.

But despite the (absolutely egregious) $1,200 price tag, the Wyatts have a chunky block heel, a slippery leather sole and very little by way of cushioning, all of which makes them terribly impractical and hard to wear for a long time, nevermind walk in.

I think we can do better—and in recent years, a number of brands have.

Below I’ve rounded up nearly a dozen men’s boots that combine the timeless look and elastic panels of traditional Chelseas with the kind of cushioning and support you’d normally expect to find in a pair of sneakers.

And unlike GQ’s rather pricey list of the best Chelsea boots, none of the pairs below cost more than 300 bucks.

Our Top Picks ↓

You can learn more about what makes each boot comfortable below, but here’s a quick summary of our favorites:

Most Comfortable Chelsea Boots for Everyday Wear:
Amberjack Chelseas
Most Comfortable Lug Sole Chelseas:
Nisolo Go-To Chelsea
Most Comfortable Chelsea Dress Boots:
Beckett Simonon Bolton
Most Comfortable Chelsea Boots for Walking:
J&M XC4 Tanner Chelsea
Most Comfortable Chelsea Rain Boots:
Blundstone 2242
Most Comfortable Chelsea Boots for Wide Feet:
Cole Haan ZERØGRAND Chelsea
Most Comfortable Chelsea Work Boots for Men:
Wolverine W10791

Table Of Contents

The Most Comfortable Men’s Chelsea Boots
The Best of the Rest ↓

Who Wrote This Article:

Irreverent Gent Founder and Editor-in-Chief Dave Bowden has been a service journalist for more than a decade, and his fashion advice and shopping recommendations have been featured in The Wall Street Journal, New York Magazine, and Men’s Health, among many others.

How We Created This List:

Comfort
& Quality

Style / Visual
Appeal

In-Person &
Online Reviews

To assess the comfort level of the Chelseas below, we took a close look at the cushioning, shock absorption and support offered by each boot’s insole, midsole and outsole.

We then compared the comfort factor to the materials and overall quality of the rest of the boot, and factored in each one’s aesthetic and visual appeal, because helping you look good and live well is kind of, like, our whole entire deal.

We were able to thoroughly test one pair, the Amberjacks, for ourselves, and factored in our personal experience with them. For the rest we did a deep dive into online reviews to get a sense of what real users had to say about the comfort and support offered by each boot.

To learn more about how we rate and review products, check out our product review and round up policy here.

**Lose the Laces (and F*ck the Foot Pain):**

The Most Comfortable Men’s Chelsea Boots

Most Comfortable Chelsea Boots for Everyday Wear: ↓

Amberjack Chelseas

Comfort Features:

Dual Density TPU outsole
Heat-activated arch support
Sheepskin lining (perforated for air flow)

Style Features:

Svelte toe shape
Available in either leather or suede
Colors Available: 6 leather, 3 suede

Why We Like Love It:

Amberjack’s Chelseas have become my new go-to everyday boot because they’re the perfect combination of sharp style and all day comfort.

From a style perspective, they’ve got a great toe shape that’s round enough to pair with jeans for a casual look, but sharp enough to look more sophisticated and smart-casual than a typical pair of casual round toe boots.

But where Amberjack really excels is in the comfort department.

The insole uses what the brand coyly calls a “fancy foam” that’s heat-activated and provides longer-lasting comfort than memory foam because it’s more durable.

(Amberjack has their own proprietary outsole and tends to be pretty stingy on the exact details/make up of their comfort tech, hence phrases like “fancy foam.”)

The dual-density outsoles look like standard rubber soles, but in the toe they use the same kind of high-performance materials found in athletic shoes, while the heel has a more supportive and durable material, like the kind used in the soles of hiking boots.

The result is a damn-near perfect Chelsea boot, especially at the sub-200 dollar price point.

Why Some Might Not:

There’s really nothing to dislike in the comfort department, but on the style front they make one choice that might alienate some people.

A lot of leather Chelsea boots (like the Nisolo and Beckett Simonon models below) have streamlined uppers that appear to be made from just a single piece of leather, resulting in seamless and classic silhouettes.

But Amberjack’s Chelsea have seams that start at the collar near the top of the elastic gussets, and run down the vamp.

Personally I don’t mind the seams because they run lengthwise down the boot, giving it a sleek and almost aerodynamic look. (Plus it’s barely noticeable on some models, especially the suede boots.)

But purists may prefer a more seamless and iconic silhouette.

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Most Comfortable Lug Sole Chelseas ↓

Nisolo Go-To Chelsea

Comfort Features:

Removable “Cellfit” memory foam insole
Shock-absorbing and treaded “Extralight” EVA outsole
Half the weight of typical leather boot

Style Features:

Mock stitching around the sole
Nice blend between an almond toe and a round toe
Colors Available: 2

Why We Like It:

The Nisolo Classic Chelsea boot is arguably their flagship product on the women’s side, and the Everyday Chelsea listed below is basically the men’s equivalent.

If this were just a list of the overall best Chelsea boots, that Everyday boot probably would have ranked higher than this “Go-To” model, but the Go-To has it beat when it comes to comfort.

Even though it’s got all the hallmarks of a good chore boot, including lugged chunky soles and a waterproof leather upper, it’s only about half the weight of comparable leather footwear, which makes it a lot more comfortable and easy to wear.

Plus it looks fantastic, particularly in the gray color, which is versatile enough to wear with a pair of jeans or a leather jacket in pretty much any color.

Why Some Might Not:

Some reviewers commented that they don’t love the faux stitching between the upper and the sole.

Usually stitching like that indicates a boot with goodyear welt construction, but sometimes boots that aren’t goodyear welted add the stitching for purely aesthetic reasons.

Foregoing the goodyear welt is one of the things that helps this one stay so lightweight, but some guys take exception to the idea of boots that only look welted.

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Most Comfortable Chelsea Dress Boots ↓

Beckett Simonon Bolton

Comfort Features:

Leather lined insoles
Vachetta leather interior lining
Heel caps made of SBR rubber (the kind often used in car tires) provide traction and shock absorption

Style Features:

Sleek (and in my opinion, perfect) toe shape
Supple, full-grain leather upper
Colors Available: 4 in leather, and 2 more in suede

Why We Like It:

If you’re in the camp that finds the Amberjacks above a little too casual, Beckett Simonon’s Bolton model is a great option.

From a style perspective, it’s got the kind of streamlined, timeless design that never goes out of style, and you can pair it with everything from a dark pair of jeans to a full suit for a variety of stylish looks.

Plus, Beckett Simonon is known for using the kind of high-quality materials usually reserved for the most expensive luxury brands, but offering them at a much lower price range because of their made-to-order business model.

In this case, that means you get full-grain calfskin leather sourced from a gold-rated tannery in Northern Italy, which is likely quite comparable to the black calf leather used in the Saint Laurent boots mentioned above, but will end up costing you less than a third of the price.

Why Some Might Not:

As a rule of thumb, the dressier the boot (or shoe), the less comfortable it will be, and the Boltons are admittedly far from the most comfortable boot on this list.

But as pure dress boots go, you’d be hard pressed to find a more comfortable high-quality Chelsea for pairing with formal looks.

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Most Comfortable Chelsea Boots for Walking ↓

Johnston & Murphy XC4 Tanner Chelsea

Comfort Features:

High-rebound midsole
Removable memory-foam cushioned insole
Temperature regulating
Waterproof leather construction

Style Features:

Versatile (and durable) oiled brown color
Colors Available: 1

Why We Like It:

Johnston & Murphy’s Tanners are kind of like the Chelsea version of a sneaker boot:

Up top they have a leather upper with an almond toe shape, but down below they’ve got the type of comfortable, sturdy soles you’d normally find on a pair of running shoes.

In addition to the sneaker-style outsole, they’ve also got Johnston & Murphy’s patented “XC4” midsole, which uses high-rebound foam that makes them a lot more comfortable than standard boots.

Why Some Might Not:

If you have big feet you might have trouble finding these in the right size.

In terms of length, they only go up in half sizes until 11.5, after which they jump straight to 12, 13, and 14. So if you’re usually a 12.5, 13.5 or 14.5, you might be out of luck here.

With that said, if you have a wider foot you might actually enjoy these. They only come in one size, which Johston & Murphy calls Medium/Wide.

It’s not quite as wide as the Cole Haan model listed below, which comes in a dedicated wide size, but it’s more generous than the Amberjacks or Beckett Simonons listed above, both of which are on the slimmer side.

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Most Comfortable Chelsea Rain Boots ↓

Blundstone 2242

Comfort Features:

Removable contoured sheepskin EVA footbed
“XRD” shock absorption in heel
Vibram outsoles for grip
Waterproof leather
Thinsulate lining for warmth

Style Features:

Round toe is casual, but classic
Colors Available: 3

Why We Like It:

Blundstone’s main claim to fame is making Chelseas that are comfortable enough to wear in (damn near) any conditions, and versatile enough to replace everything from desert boots to cowboy boots in your wardrobe.

They make a wide range of Chelseas, but the 2242 “all-terrain thermal” model is one of their best for both comfort and water resistance.

In addition to waterproof leather, it’s made with Thinsulate, which will keep your feet as warm as they are dry, a Vibram rubber outsole and a shock-absorbing heel.

Why Some Might Not:

While Blundstone is generally regarded as a good boot maker, some users have suggested that the manufacturing quality dipped when they moved their factory from Tasmania, Australia to Thailand.

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Most Comfortable Chelsea Boots for Wide Feet ↓

Cole Haan ZERØGRAND Chelsea

Comfort Features:

ZERØGRAND cushioning
Side gore
Waterproof
Available in Medium or Wide width

Style Features:

High-quality, supple leather
Colors Available: 3

Why We Like It:

This one from Cole Haan’s “Zerogrand” line is another sneaker-like Chelsea that has a thick, athletic-style outsole mounted under the leather upper, which provides plenty of traction, comfort and support.

What’s nice about Cole Haan is that they offer a lot of their shoes in three distinct widths: narrow, medium and wide.

The system for measuring shoe widths is kind of weird (you can read a good breakdown of it here), but the main thing to know about Cole Haan is that their “wide” widths go up to size EE, also sometimes called EW (because, again, the way shoe widths are measured is bizarre).

Why Some Might Not:

These ones are kind of in-between a dress boot and a casual boot, which some guys might not love.

If your personal style tends to lean more towards dressier smart-casual pieces, you’ll probably be better off with the Amberjacks listed above, which have the same level of comfort but come with more of a pointed toe, giving them a more sophisticated look.

On the flipside, they might actually be too dressy if you’re not trying to make a style statement, and just want a casual pair of comfortable sh*t kickers.

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Most Comfortable Chelsea Work Boots for Men ↓

Wolverine Men’s W10791 Construction Boot

Comfort (and Work) Features:

“EPX” anti-fatigue
Honeycomb heel footbed
Cushioned midsole
Composite toe ASTM F2413-11 M I/75 C/75 EH
Slip Resistant

Style Features:

Combo of a classic, round toe shape and 100% full-grain leather upper makes them handsome enough to wear both on and off the job site
Colors Available: 2

Why We Like It:

And speaking of comfortable sh*t kickers, this construction boot from Wolverine is a good choice for the job site because it combines some serious comfort and safety features with a classic, versatile style.

It’s got a cushioned anti-fatigue insole and “honeycomb” footbed that provide plenty of comfort for long days on your feet, and comes with pull tabs at the top of the elastic gores that make it comfortable not just to wear, but to slip on.

Why Some Might Not:

Like most construction boots, this one is built more for utility than aesthetics. While it still manages to score plenty of points in the style department, one place where it’s severely lacking is in the color department.

There are only two colors to choose from, and – spoiler alert – they’re both pretty similar shades of brown.

Which is a real shame, because these are actually pretty stylish as construction boots go, so it would be nice if you could get the comfort features of this model in a pair of tan or black Chelsea boots.

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