The Best Chelsea Boots for Men

We independently evaluate the products and brands we recommend, and may receive compensation if you click on links within this post. Click here to learn more.

It doesn’t take a genius to understand why style-conscious guys would want to find the best Chelsea boots on the market. 

No other men’s boot style can match Chelseas’ unique combination of convenience, style, versatility and timeless appeal

While boots with elastic panels can be traced all the way back to the Victorian era, modern Chelseas established their bonafides – and their name – in London in the ‘50s and ‘60s, when British tastemakers like the Rolling Stones popularized the ankle boots for men (and model Jean Shrimpton did the same for women). 

Man wearing blue jeans and chelsea boots
Sharp style and no laces? Yesssir.
[image: Michael Fenton / Unsplash]

In addition to a pretty impressive style pedigree, you really can’t beat the laceless design and elastic side panels of Chelseas when it comes to convenience.  

I love a good sh*t-kicking pair of lace-ups as much as the next guy, but there’s just something so satisfying about sliding your foot into a pair of Chelseas and being ready to go. 

But if Chelseas have a flaw, it’s that the market has been flooded with a metric sh*t ton of “affordable” (i.e. cheaply made) models in recent years, which makes it hard to distinguish the well-made and worthwhile Chelseas from the cheap knock offs. 

To help you get the most bang for your buck, in this post I’ve put together a list of the best Chelsea boots for guys, and broken it down into categories so you can find the best pair of boots to suit your budget, tastes and style. 


The (Absolute) Best Men’s Chelsea Boots

Breaking Down the Best Chelseas for Men
(in Damn-Near Every Category Imaginable)

Best Dress Chelsea Boots for Men ↓

Beckett Simonon Bolton

Bolton Chelseas
Rating: 

5 Stars, 368 Reviews

Features:

✅ Sophisticated, almond-shaped toe box 
✅ Full-grain, supple and smooth calfskin leather upper 
✅ Vachetta leather lining provides temperature regulation and sweat absorption 

Promising Review

Excellent quality Chelsea with leather sole… I ended up buying two and both run true to size. 

Beautiful and super great quality and craftsmanship. Definitely buy more.

– Mark F.

Check Price ➤

Bruno Magli Byron

Bruno Magli Chelsea
Features:

✅ Italian-made boot 
✅ Made from black calf leather
✅ Rubber outsole provides strong grip, while toe shape provides classic style of a dress shoe

Check Price ➤

Ted Baker Lineus Chelsea

Ted Baker Chelsea
Features:

✅ Top-grain leather 
✅ Available in both black and brown
✅ Extra touch of style thanks to Ingrained pattern on elastic gusset

Check Price ➤

Best Chelsea Work Boots for Men ↓

Georgia Boots Eagle One

Georgia Boots Eagle One
Rating: 

4.9 Stars, 21 Reviews

Features:

✅ ASTM F2413 protective toe classification
✅ ASTM F2413 electrical hazard standard
✅ Cushioned EVA midsole
✅ Waterproof

Promising Review

I really need a comfortable shoe as I am on my feet all day. A back injury makes it difficult to tie my shoes so these looked like a great option. I was so right! 

These boots were super comfortable from the moment I slipped them on. The soles have exceptional cushion and the slip on design still kept the boot snug against my ankles preventing it from flopping around. These are my favorite boots by far!!

– Shawn B.

Check Price ➤

Carhartt Men’s Wedge 5″ Chelsea

Carharrt Chelseas
Rating: 

4.3 Stars, 337 Reviews

Features:

✅ Soft toe work boot 
✅ Insite anti-fatigue footbed for all day comfort 
✅ Classic look can be worn on or off the job site 

Promising Review

I would say they fit just a little bit on the large side, which is good for pull ons. 

Easy on and off and I like the strap is sort of half way down the back of the boot so your jeans don’t get hung up on them. Certainly would buy another pair. Very comfortable

– Zeke

Check Price ➤

Ariat Groundbreaker Chelsea

Ariat Chelseas
Rating: 

4.4 Stars, 1,508 Reviews

Features:

✅ Rated as ASTM F2413-11 M I/75 C/75 EH
✅ 100% leather upper
✅ Four Layer Rebound insole for extra comfort

Promising Review

Love them. My first pair of slip on work boots, have always used laced boots before, and use them every day working in an industrial plant. 

They were comfortable from day 1 and seem to hold up well after several hours and days of walking, climbing, etc. great buy!

– John P Aparicio

Check Price ➤

Best Waterproof Chelsea Boots for Men ↓

Cole Haan Men’s Zerogrand Chelsea Waterproof Boot

Cole Haan Chelseas
Rating: 

4.6 Stars, 526 Reviews

Features:

✅Fully waterproof outer layer
✅Rubber forefoot and heel pods on the outsole for traction 
✅Available in regular and wide fit 

Promising Review

These boots are beautiful and extremely comfortable! I love them so much that I almost bought a second pair while my 1st pair were still new so that I could begin wearing them after the originals were worn. 

– Gemorial

Check Price ➤

UGG Men’s Biltmore Chelsea Boot

Ugg Chelseas
Rating: 

4.5 Stars, 1,888 Reviews

Features:

✅Fully waterproof and seam-sealed construction
✅White spider rubber outsole (good for traction on wet ground) 
✅Comes with Ugg’s flagship “enerG” comfort system insole 

Promising Review

Absolutely love the comfort of these boots. Being waterproof, I was a bit worried my feet would sweat like crazy, but they don’t. Very comfortable for all day wearing. Highly recommend.

– Brian Grundhauser

Check Price ➤

Wolverine I-90 Waterproof Boot

Wolverine Chelseas
Rating: 

4.4 Stars, 1,217 Reviews

Features:

✅Breathable waterproof membrane with moisture wicking mesh
✅EPX anti-fatigue footbed for long-lasting comfort and support 
✅High abrasion TPU SR lug outsole

Promising Review

So far they are holding up well. I’m a plumber so waterproof was a big part of my decision to buy these and so far so good.

– Robby Watson

Check Price ➤

Best Casual Chelsea Boots ↓

Preston Chelsea Boots

Preston Chelseas
Rating: 

5 Stars, 50 Reviews

Features:

✅ Made from full-grain leather calfskin sourced in Northern Italy
✅ Round toe shape is casual and versatile
✅ SBR rubber heel caps provide traction, durability and shock absorption

Promising Review

These are world class. As good if not better than boots from Europe at 3x the price. Do not hesitate. They are the real deal.

– Christopher G.

Check Price ➤

Amberjack Chelsea 

Amberjack Chelseas
Rating: 

4.8 Stars, 305 Reviews

Features: 

✅ Heat-activated arch support that’s more durable than memory foam
✅ Svelte toe shape and athletic outsole make for excelletn combo of casual and comfortable
✅ Sheepskin lining makes them warm enough for fall and winter months, without being too bulky

Promising Review

My new Amberjack Chelseas are a game changer… They are extraordinarily comfortable right out of the box! 

They look great, especially because of the low-profile soles… I don’t think I have felt better about a wardrobe purchase I have made in a while. Amberjack have knocked it out of the park!

– D.P.

Check Price ➤

Frye Tyler Chelsea

Frye Chelseas
Rating: 

4 Stars, 20 Reviews

Features:

✅ Lived-in, vintage feel adds ruggedness and character
✅ Blake construction
✅ Leather outsole and rubber toplift provide traction

Promising Review

Looks great, extremely well made and comfortable. Requires a little time to break in but definitely worth the wait. Highly recommend!

– Michael T.

Check Price ➤

Best Chelsea Boots for Wide Feet ↓

Allen Edmonds Discovery

Allen Edmonds Chelseas
Rating: 

4.3 Stars, 69 Reviews

Features:

✅ Available in B, D and EEE widths
✅ Made in the USA
✅ Relaxed fit provides more room for wide feet

Promising Review

I’ve had these boots for a few months now, and the longer I have them the happier I am. They are very high quality with a perfect blend of support and comfort…

My “true” size is 11E in AE shoes but the 11D was plenty roomy. (I am customarily an 11.5+ in other brands, so I find AE to run larger in general.)

– SloopyJ

Check Price ➤

Johnston & Murphy XC4 Maddox

Johnston and Murphy Chelseas
Rating: 

4.8 Stars, 47 Reviews

Features:

✅ Comes with removable footbed that changes a medium to a wide
✅ Dual-density, XC Foam and rubber sole provides good grip
✅ Full grain leather upper

Promising Review

Love these Chelsea boots. My first pair, and I hope to have them for some time as a staple to my wardrobe. The look, fit, and cushioning out-of-the-box was amazing.

– Clinton

Check Price ➤

Clarks Clarkdale Easy

Clarks Chelseas
Features:

✅ Available in either medium or wide fit
✅ Six colors to choose from
✅ Classic, versatile style

Check Price ➤

Best Chelsea Boots for Walking ↓

Johnston & Murphy XC4 Tanner

Johnston and Murlph Chelseas
Rating: 

4.8 Stars, 17 Reviews

Features:

✅ High-rebound XC Foam midsole makes them easy to wear for a long time
✅ Removable, memory-foam cushioned insole with contoured arch support
✅ Svelte toe shape (so you don’t need to sacrifice style for comfort)

Promising Review

Amazing comfortable boots! They are true to size and supper comfortable for walking all day.

– Yahaira

Check Price ➤

Clarks Hinsdale Up

Clarks Chelseas
Rating: 

4.3 Stars, 3Reviews

Features:

✅ OrthoLite Hybrid foam footbed
✅ Shock-absorbing EVA sole
✅ Waterproof and warm enough for winter months

Promising Review

Other reviews suggested these boots run small, so I ordered a half-size larger than what I would typically order- that proved just right.

A bit tight in the toes, but has loosened up with a short amount of wear.

Good value for a good looking, waterproof boot.

– CSBL

Check Price ➤

Bruno Magli Romeo Twin Gore 

Bruno Magli Chelseas
Features:

✅ Combines Chelsea style with comfy sneaker sole
✅ Hand-burnished Italian calf leather upper
✅ Available in black or brown

Check Price ➤

Best Winter Chelsea Boots for Men ↓

Keen Anchorage 3 Insulate Snow Boot

Keen Chelseas
Rating: 

4.5 Stars, 2,826Reviews

Features:

✅ Water and snow proof
✅ Rubber outsole with 4mm multidirectional lugs provide great grip
✅ Dual-density PU footbed with arch support

Promising Review

I absolutely love these boots and this is my third pair. My feet have NEVER been cold during the Colorado winters working on my ranch and I have walked over 1000 miles in my old pair and they still are holding up great… 

Just a great winter boot all around. Great traction in the snow and warm toes!!! 

– Happy

Check Price ➤

Ugg Men’s Hillmont 

Ugg Chelseas
Rating: 

4.4 Stars, 115 Reviews

Features:

✅ Wool lining
✅ Waterproof leather upper with seam-sealed construction
✅ Weather Rated to -32˚C

Promising Review

Perfect for winter. Really comfortable and very warm.

– SR

Check Price ➤

Dr. Martens Men’s 2976 Wintergrip Snow Boot

Dr Martens Chelseas
Rating: 

4.5 Stars, 199 Reviews

Features:

✅ Wintergrip sole with EVA grooved cleats for traction
✅ Goodyear welt construction
✅ “Snowplow” water-resistant leather designed for snow

Promising Review

Wintergrip is no joke. When you live in a ski town, there’s ice and snow on every street from November through April. Having footwear with some ice specific traction is helpful, having that footwear pass in a restaurant or “casual” business meeting is even better…

Also comfortable and warm.

– Michael Faas

Check Price ➤

Best Lug Sole Chelsea Boots for Men ↓

Silva Chelsea Boots 

Silva Chelseas
Rating: 

4.9 Stars, 82 Reviews

Features:

✅ Hits the sweet spot between rugged and refined
✅ Water-repellent, pull-up leather upper
✅ Open cell memory foam footbed

Promising Review

I’m surprised at how light they are. It’s like walking on pillows.

– Miles K.

Check Price ➤

Blundstone BL566

Blundstone Chelseas
Rating: 

4.4 Stars, 1,994 Reviews

Features:

✅ Thinsulate insulation
✅ Genuine shearling footbeds
✅ Broguing around the elastic panel is a great addition

Promising Review

These boots are super comfortable and surprisingly lightweight. Zero break in time, I was able to put them on and go! I have a wide foot and these fit perfectly. 

Plenty of room in toe box and good arch support. Lugged enough to tread in winter weather without slipping. Water and weatherproof, especially with proper maintenance.

– Joe Mama

Check Price ➤

M.Gemi Dario 

MGemi Chelseas
Features:

✅ Great combo of style and ruggedness
✅ EVA rubber lug sole
✅ Handmade in Tuscany, Italy

Check Price ➤

Best Rugged Chelsea Boots for Men ↓

Georgia Boot Carbo-tec Lt Chelsea

Georgia Boots Chelseas
Rating: 

4.4 Stars, 14 Reviews

Features:

✅ SPR full-grain leather
✅ Goodyear welt construction
✅ Heat, chemical, abrasion, and slip-resistant outsole

Promising Review

They are great boots. They check off a lot of must have features for me (goodyear welt, waterproof, oil and slip resistant). 

Make sure they fit a little snug when you first get them because as the heel sets in they loosen up a bit.

– Kieth H.

Check Price ➤

Blundstone Classic 550

Blundstone Classic Chelsea
Rating: 

4.5 Stars, 644 Reviews

Features:

✅ Leather upper is 2.5 mm thick
✅ Twin-needle reinforced stitching with high-tensile-strength thread
✅ Dual-density thermopolyurethane outsoles

Promising Review

Fit perfectly right out of the box. No break in time needed. I reach for these every single day. I have purchased them in another color now because I love them so much.

– D.E.S

Check Price ➤

Ariat Rambler

Ariat Chelseas
Rating: 

4.6 Stars, 563 Reviews

Features:

✅ Designed for outdoor work in tough conditions
✅ Duratread outsole
✅ Great, modern alternative to cowboys

Promising Review

These boots are awesome! I have absolutely punished mine, even though they are nice enough to wear as a daily. I love that they slip on so easily. 

I have toured construction sites, done yard work and even shoveled snow in these. I will definitely buy again.

– Cory

Check Price ➤

Best Cheap, Affordable & Low End Chelsea Boots for Men ↓

Bruno Marc 

Bruno Marc Chelseas
Rating: 

4.2 Stars, 5,765 Reviews

Promising Review

I have more than the average number of shoes for a guy and I seriously find myself wearing these a lot. They are really comfortable but I am also pretty lazy and love slip on /off shoes and these are perfect. 

I ended up buying a second paid in the same black color and will buy a brown pair as well. There are of course nicer and fancier Chelsea boots out there but for the price I was pleasantly surprised and I highly recommend these

– JRS

Check Price ➤

Steve Madden 

Steve Madden Chelseas
Rating: 

4.5 Stars, 1,002 Reviews

Promising Review

My favorite pair of shoes. This is my second pair since I wore out my first ones. The quality is good and they are very comfortable.

– Nick K.

Check Price ➤

Jousen

Jousen Chelseas
Rating: 

4.3 Stars, 3,763 Reviews

Promising Review

Great product for the price, lasts as long as I would expect. I’m hard on all shoes! Just received another pair this week. They look and were packaged great!

– BrendenMO

Check Price ➤

Best Chelseas By Color ↓

Where to Find the Best Black Chelsea Boots for Men

Amberjack
Amberjack Black Chelseas

If you’re specifically looking for a well-made pair of chelsea boots in black, Amberjack is probably your best option. 

They offer three different black models in two different types of boot material: 

  • the black leather Obsidian model, which has a more formal style; 
  • a pair with a black suede upper that they call the Midnight, which is both handsome and reminds me of Agent Michael Scar’s Threat Level Midnight
  • and a black leather pair with a white sole, the Onyx, which has a more casual look 

All three pairs have the same classic silhouettes and comfortable sole that make Amberjack one of my favorite brands, and all would pair equally well with a black leather jacket

The Obsidian and Midnight could both be worn on formal occasions, but it’s worth noting that the white sole of the Onyx makes it look a little more like a casual shoe, so it’s tougher to pull off with a full suit. 

Check Out Amberjack ➤

Where to Find the Best Brown Chelsea Boots for Men

Beckett Simonon 
Beckett Simonon Brown Chelseas

The main reason that Beckett Simonon is the best place to turn for brown Chelseas is that they have a ton of options available.

First and foremost, they offer five different Chelsea models (well, six if you count their zip-up boot, which I don’t because it doesn’t have the elastic insert). 

Their Chelsea’s range from dressier formal options with a pointed toe and sleek silhouette, to more casual, round-toe boots with chunky soles that would look great with a classic white t-shirt and jeans. 

And even when filtering for brown colors, you still have a number of options to choose from. 

They offer four different shades of brown leather, and two shades of brown suede, making it pretty easy to find the perfect pair to suit your personal style game. 

Check Out Beckett ➤

Where to Find the Best Tan Chelsea Boots for Men

Oliver Cabell 
Oliver Cabell Chelseas

For tan Chelseas I recommend Oliver Cabell, whose Lion model may be one of the best casual boots on the market. 

In addition to coming in a perfect, sandy shade of tan, they have an Italian crepe sole and stitch-down construction that make them as well-made as they are stylish. 

They’re perfect for everyday wear, especially during the warmer spring months, when lighter shades like tan are great for pairing with lighter shades of blue jeans or green chinos.

(Check out my full spring style guide for more advice on nailing the warm(ish) weather look.) 

Check Oliver Cabell ➤

Best Chelseas By Material ↓

Best Leather Chelsea Boots for Men

Best Dressy Leather Chelseas

Beckett Simonon Bolton
Beckett Simonon Bolton Chelseas
Rating: 

5 Stars, 368 Reviews

Promising Review

Excellent quality Chelsea with leather sole… I ended up buying two and both run true to size. 

Beautiful and super great quality and craftsmanship. Definitely buy more.

– Mark F.

Check Price ➤

Runner Up

R.M. Williams Chinchilla
RM Williams Chelseas
Check Price ➤

Best Casual Leather Chelseas

Allen Edmonds Grafton Chelseas 
Allen Edmonds Chelseas
Rating: 

4.2 Stars, 27 Reviews

Promising Review

These shoes look great, particularly with jeans, and they feel like slippers. Even after wearing them all day I am reluctant to take them off, which is a rarity for me.

– Gary J.

Check Price ➤

Best Suede Chelsea Boots for Men

Best Dressy Suede Chelseas

Suede Bolton Chelseas 
Suede Bolton Chelseas
Rating: 

4.9 Stars, 69 Reviews

Promising Review

High quality shoe with great material. I own a couple of chelsea boots and often look for slim/bespoke fitting ankles and overall a great foot shape. 

This definitely hits that mark and I’ll likely be purchasing only from here.

– Ryan V.

Check Price ➤

Best Casual Suede Chelseas

Astorflex Chelsea Boot
Astorflex Chelsea Boot
Rating: 

4.6 Stars, 617 Reviews

Promising Review

I absolutely love my new Chelsea boots…very stylish and comfortable…, oh yeah, I would definitely recommend them to anyone.

– Donald B.

Check Price ➤

More Resources ↓
More Advice on Stylish (and Sh*t-Kicking) Men’s Boots:
More Advice on Stylish Men’s Shoes:
Banner photo: Beckett Simonon; Illustration: Irreverent Gent

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.