For the longest time, I positioned myself quite actively against Chelsea boots. Boots should have laces, I said! But Chelsea boots do not have laces. So there I was, avoiding Chelsea boots at all costs, without a true shred of experience wearing them.

But then I did a collaboration with the excellent Indonesian bootmaker Benzein, who does many things quite well, but in a lot of ways specializes in Chelsea boots (and some very fine engineers…but man are they good at Chelseas). And I loved them.

So here we are, with me writing about how I actually was an idiot previously, but am now a smart person. Or at least smart enough to realize that Chelsea boots can be pretty great.

Chelsea Boots

A Brief History of Chelsea Boots

The full story of the Chelsea boot’s history has already been told by our friend Jesper over at Shoegazing, and you should absolutely go read it.

But the extremely short version is: Queen Victoria’s shoemaker J Sparkes-Hall made her some elastic-gusseted balmoral boots in 1837, and boyyyyyyy did ol’ Vic love ’em. Then the Beatles wore them, and they got named the Chelsea boot because everyone in the mod-happy London neighborhood got in on the style. And then they got adapted to just about every use in the world.

That’s the story. Seriously, go read Jesper’s version.

Alright So What Makes a Chelsea Boot a Chelsea Boot?

One simple answer is: Chelsea boots are 100% laceless, but then again, so are other boots (engineers, Jodhpurs, side zips, ropers, etc). The defining characteristic of a Chelsea boot is the elastic gore that’s stitched into an open part of the pattern around the ankle, which stretches to allow your foot to enter the boot, and then cinches everything back into place once it is. So they, you know, stay on.

While there are some very nice tall Chelseas on the market, and I’d even consider short-boy Romeos like these from Wesco to be Chelsea boots in a way, generally Chelseas clock in around 5 to 6 inches tall, and most tend to feature a heel—although I personally feel that many of them look great on a wedge sole as well.

And that’s it! Pretty much as simple of a boot pattern as you can get, although there are endless variations to them in terms of pattern (of course there are also different soles, welts, heights, etc), largely around the shape of the pattern opening for the gore. The presence of one or two (or zero!) pull-tabs on each boot is also in flux. And then we get to wholecut vs. non-wholecut, aka, making the entire boot’s upper out of one single piece of leather, or…not.

rm williams comfort craftsman

Wholecut Chelsea Boots

The wholecut Chelsea is without question the pinnacle of the form. Of course everything else has to be right—last shape, sole choice, finishing, overall pattern and balance. But when they’re done right, a wholecut Chelsea is just an absolutely beautiful boot, with no vamp/quarter seam (generally sitting right under the gore opening) to break up the long swoop of leather that runs all the way to the back of the boot, where everything is stitched together (and sometimes covered up with a backstay panel).

If it was easy, or efficient in terms of leather yield, everyone would make wholecut Chelseas. It is not either of those things, so most do not. That said, this does not in any way mean that non-wholecut Chelseas are bad boots! Most of my personal favorites on my shelf are actually not wholecuts. There are pattern-shortcut-hacks on other styles of shoes that can be legitimately egregious; a nicely executed non-wholecut Chelsea (generally) does not fall into that category.

What Makes a Chelsea Boot a GOOD Chelsea Boot?

To me, two key factors combine to create a truly great Chelsea boot: the last (the wooden or plastic form around which all shoe are made and give them their shape) and the pattern.

Let’s talk about the pattern first. Most are fairly similar at first glance, but pretty much every maker has its own pattern that’s somewhere between slightly and majorly unique. First off, I don’t personally believe in any sort of toe caps or brogueing or any other decorative frills on a Chelsea boot. Some get pretty close to looking good, but I just believe there are plenty of other boots and shoes on which that kind of adornment looks more rightfully at home on—plus the overall silhouette balance always feels off to me.

And even on more classically “clean” Chelsea patterns, when things get overly aggressive—a gore opening that’s just too wide, or too big overall, or too, um, creative (really darn square?), for instance—I tend to lose interest. It’s a simple pattern, and to me, it’s best kept that way, with a few exceptions.

And then, the most crucial determining aspect of Chelsea boot excellence: the last. When you look down at a pair of lace-up boots or shoes, you see a lot of things: the laces, the eyelets, the various panels of the pattern. Perhaps some brogueing, or a toe cap. A hand-stitched apron sitting over the toe box. Maybe various panels in contrasting colors or textures.

On a Chelsea boot, you’ve got the leather and the last. The leather really more than anything is a preference thing, and should match your desired use—most Chelsea boots look wonderful in all manner of reverse and smooth leathers, from dressy calf to suede or a rugged oil-tanned roughout, and even a pebble or hatch grain can do the trick at times if that’s what you’re looking for.

But no matter the leather, the last is what you see when you wear them. Even a Chelsea boot made with the world’s greatest leather (the one that speaks directly to you) that doesn’t offer a proper last shape simply does not deliver the appeal it should, or present something aesthetically pleasing to glance down at. Chelsea boots can easily turn into formless blobs if paired to the wrong last—but can be something truly, simply beautiful if that vamp is nice and snug and gets some wonderful little rolls going. And you deserve better than a formless blob on your feet.

Now this is not to say there is a “perfect” Chelsea boot last for everyone. Any shoe last decision is a personal one. I tend to prefer more round-toed lasts to an extent, but to me a Chelsea boot needs to have, at the very least, something approaching an almond-shaped toe, aka, not something you’d find on, say, a work boot. More anatomical Munson-type lasts? Those also just feel wrong in most cases. Many Chelsea lasts can get quite pointy and elongated; that’s not really for me, but I absolutely understand why some people are into them.

A chisel/square-toe last is a very popular Chelsea boot last, and the signature of Australian Chelsea boot maestros R.M. Williams, the nearly 90-year-old Australian maker that many consider to be the best Chelsea boot maker in the world. Even when artfully done, there’s no not noticing the distinctively brutish beauty of a chisel toe Chelsea, which, again, is kind of the whole point; give me something to marvel at when I look at my feet. The only question is whether or not it’s for you.

A Quick Note on Chelsea Boot Sizing

It’s tough! Size too big, and your foot doesn’t stay locked in place. Size too small, and you get the standard “damnit I sized too small” discomfort issues, and might not even be able to get in and out of them very easily. Which is a pretty big deterrent for any boot that you wish to wear on your feet, and an even worse one for a boot whose value prop is very much tied up in “these things are a snap—you don’t even have to take the time to tie them up!”

As always, if you can try on the pairs you’re interested in at a brand shop or multi-brand retailer, absolutely do it. And try out a number of sizes and widths if possible. The thing about that Chelsea boot vamp is that a couple steps can really crease the leather, but even pulling them on and off can do the same. So do the respectful thing and be gentle if possible. Also don’t forget when trying them on that the midsole in most cases will likely flex more and more over time, decreasing any heel slip.

The most important things to think about: is the widest part of the ball of my foot aligned with the widest part of the last? Are my toes getting pinched? Am I sliding around like crazy in them? While not every Chelsea boot is not going to fit every foot, in any size, the nice thing is: there aren’t as many variables as with other footwear. If you get a nice Chelsea boot fit, you just kind of know.

Five Chelsea Boots I Have Come to Love

Grant Stone Chelsea Boot

Grant Stone Chelsea in Chocolate Calf: $328

My Grant Stone Chelsea boots have something of a junior version of an R.M.-style chisel toe—the toe itself takes a tapered, semi-elongated round approach, but the welt and midsole get squared off to create a lower-impact version of the same visual effect. These, while not necessarily a true dress Chelsea, are the dressiest by far in my collection, but can flex them down to casual fairly easily (although I wouldn’t feel right wearing them to like, Home Depot. I always manage to scuff my boots a lot at Home Depot).

Grant Stone Chelsea Boot

The pattern is wonderfully straightforward, letting the last and leather—a superb Annonay calf that creases quite tightly and has developed a bit more depth of color with time—do the talking, as they should. And they manage to hit the sweet spot of easy-on/easy-off while still largely providing a nice snug fit around the ankle and heel. Of course, the Goodyear welt construction is spot-on, and at just over $300, these may just be the best-value really nice Chelsea boots on the entire market.

Sizing: I went .5 down from Brannock and they fit well if a touch snug up front with dress socks, although they’ve felt better and better as time has gone on. Before long, Grant Stone will offer these in an E width; myself and others with a high instep or wide feet will be very, very happy.

tangier by ledbury kudu chelsea boot

Tangier by Ledbury Kingstowne Chelsea in Waxy Kudu: $425

By far my most worn Chelsea. Ledbury’s main game is top-notch buttondown shirts and other menswear, but they teamed up with shoemaking shadowforce/Shoecast legend Ron Rider to manufacture these in Italy, and man did they get it right. At $465, they’re at the upper end of the price scale for my own personal Chelsea collection, but worth every dollar and probably a few more.

tangier by ledbury kudu chelsea boot

At first the grey-blue kudu leather seems like a loud one, but then you wear it with anything fairly casual and you realize it goes with…anything fairly casual. The last on these is just perfect for my taste, featuring a nicely rounded toe that almonds out just perfectly.

Made with storm-welted rapid construction, it’s a very sturdy boot that feels more like a Goodyear-welted boot in terms of solidity, but weighs in slightly lighter than its silhouette would indicate. A nicely grippy microstud sole makes them ready for just about any action. I truly love these boots.

Sizing!: I took .5 sizes down from my D-width Brannock, and they are perrrrrfect.benzein chelsea boot rare wine reverse chamois

Benzein x Stitchdown The Seventh Chelsea in Rare Wine Reverse Chamois: ~$450

The first Chelsea boot that really nabbed my heart was a gamble. I wanted to do a collaboration with Indonesian maker Benzein, who has carved out a well-deserved spot with one of the very best wholecut Chelsea boot patterns in the entire world. So we went for what they did best, and used a mysteriously colored Rare Wine reverse chamois from Chicago’s Horween tannery. And guess what: it really worked out. These exact boots were a limited run, but Benzein’s options are basically limitless.

Hand-welted with precision, beautifully finished, and perched atop a Dr. Sole Supergrip half-sole, this to me is the definition of a rugged/classy Chelsea boot that you’re not afraid to rough up, and can pull all sorts of duty. Benzein’s Kujang last—while a bit too shapely and severe for me personally to desire on, say, a service boot—is absolutely stunning in Chelsea form, with all the curves in the right places. It’s the definition of giving you something nice to look at when you peek down.

benzein chelsea boot rare wine reverse chamois

While Benzein does some ready-to-wear work, most of their business is made-to-order, whether you decide to go with a makeup they’ve already made for someone else, or to turn it loose with your own boot-magination. Benzein may have a bit of this leather left, but I highly recommend you check out their Instagram feed for more inspiration. Their Chelsea boots run around $400+

Sizing: I took a 43 at 11D Brannock, and they fit really nice and snug with dress socks—but my somewhat high instep has made it a bit of a chore to get them on and off. More than I’d like. If I got another pair on the Kujang last I’d probably go up a full size to 44 and wear with thicker socks. Benzein can also make adjustments to make entry/exit easier, which is incredibly cool.

jim green stockman chelsea boot

Jim Green Stockman Chelsea: $119

South Africa’s Jim Green—who sources literally every single component from the country—is not here to sell you beautifully fancy Chelsea boots. These things are 100% work boots, and that’s exactly what I use them for. The heavily lugged sole—attached via a simple stitchdown construction—has a ton of grip, and these are the easiest-in, easiest-out of the bunch, but my foot’s still locked in pretty effectively.

jim green stockman chelsea boot

I said earlier that a more anatomical Chelsea boot last just doesn’t work. Well Jim Green uses one and I simply don’t care! There’s too much shit to haul around the yard in them to be worrying about that, they’re quite comfortable, and I’ve gotten used to the look. And at $119, they’re an incredible value for a boot that can take whatever you throw at it (although maybe don’t throw really sharp swords at it).

Sizing: 11 worked for me, especially with big thick socks. These aren’t really made to be a foot-hugger, and again, they feel legitimately comfortable and stay on the feet quite well despite being a touch roomy.

cobbler union benjamin UR chelsea boot

Cobbler Union Benjamin uR in Tobacco Suede: $425

Also in the running for Classiest Chelsea Boot Ben Owns is the Benjamin uR in tobacco suede from Cobbler Union, the Atlanta-based company that manufactures excellently priced, wonderfully finished Goodyear welt boots and shoes in Spain.

The suede is PHENOMENAL—classy as all get out when new, but like all good suedes, it takes a beating quite gracefully. The last is similar to the Tangier boots, but slightly more almond-y in the toe, which makes the whole package a touch dressier. Which is perfect for me—not TOO fancy, and can pull upticked casual duty with easy, but still definitely packing a serious hit of overall class.

cobbler union benjamin UR chelsea boot

They’re noticeably taller than the Benzeins, but also have a lower heel height, which makes for overall more total boot wrapping your ankle and above, which is, well, comforting (although honestly all these boots are of a similar enough height that it doesn’t REALLY matter). I also really dig how the upper pattern and gore interact—to me it’s a perfect height/width, and are plenty easy to get on and off.

In terms of finishing, I’m gonna go ahead and say the Cobbler Unions are tied with the Grant Stones and Benzeins, while the other two boots are designed and built to be more rugged/casual anyway. But it’s just a really beautifully constructed boot, and the lightest weight of the bunch, although it does nothing but inspire long-term confidence in how they’ll hold up. Really just a damn handsome boot.

Sizing: I took a 9.5 UK/10.5 US and they fit really quite nicely with dress socks. MAYBE would consider going up half a side for just a little more space up front but I’m quite happy with the fit as is.

Other Chelsea Boots You Should Absolutely Consider

RM Williams Craftsman Chelsea Boot

R.M. Williams Craftsman: $495

The icon of Chelsea icons, R.M.’s Goodyear welted wholecut masterpieces—evolved from a boot originally designed for life in the Australian Outback—remain truly distinctive. Chisel-square toe, red leather sole (there are plenty of other options available too), and just a perfect pattern. Very hard to go wrong.

viberg Chelsea Boot Snuff Calf Suede

Viberg Chelsea Boot: $740+

The 90-year-old Canadian maker—which has grown from a true workboot company into probably the most influential heritage boot maker around—has refined its Chelsea boot over the years, like so much of its lineup.

clarks chelsea boot

Clark’s Clarkdale Gobi Chelsea Boot: $170

I’ve somehow never owned a pair of Clark’s, and tend to think that for their desert boots, there are superior options (even if they cost a bit more). But I have to say, especially for the price, these guys just work. Really nice simple pattern—kind of amazing how hard it is for so many others to just…do this—nicely rounded, pleasing last, and, I would imagine, ample comfort.

crockett & jones chelsea boot scotch grain

Crockett & Jones Chelsea Boot 11: $700

Of course one of Northampton, England’s oldest shoemakers has a range of plenty-classy Chelsea boots in suede and supple calf leather, but I love how they embrace their country-boot roots with these lug-soled, Scotch-grain you-know-what kickers.