Styling Chelsea Boots

While the Chelsea boot is a style that’s over 150 years old, it’s become a contemporary favorite for guys today. The boot’s inherent simplicity lends itself well to a variety of looks, and if the several celebrity co-signs weren’t enough, we can safely say that it’s a very easy boot to assimilate into your closet.

They Should Fit Snug, But Not Tight

Chelsea boots look beautiful for their smooth, slip-on design, but that also means you need to get the sizing absolutely right. Ignoring this will result in boots that will hurt your feet so much, you’ll never wear them again.

When you’re looking to buy, it’s best to try on the boots—especially because sizing and shape varies between brands and models. Regardless, you want a snug fit, but not one that pinches your toes. Because there are no laces, you certainly can’t tighten the boot if you’re stepping out of it, but you also can’t loosen it up if it feels too tight on the sides. Did you know shoes come with widths as well as length sizes? Getting a wider or thinner shoe size may be the trick as opposed to sizing up or down. For those with high arches, be particularly aware of the sloping from the top of the boot to the toe, as this detail changes the fit drastically, but this varies by style and brand.

Learn The Different Styles Of Boots Out There

To state the “standard,” a traditional Chelsea boot is made of black (or occasionally brown) boxcalf leather, with a leather sole. That said, over time, variations have emerged that aresimilar to the Chelsea boot, but wouldn’t technically go by that name.

There are subtle differences that have cropped up to cater to a contemporary market. Here are some of the basics:

A Commando Sole

(basically a rubberized sole with treads) is common, especially for people who are looking for a Chelsea boot that can handle snowstorms and tough weather.

Jodphur boots share the horse-riding origins with the Chelsea boot, but have a wrap around buckle closure instead of elastic side panels. As mentioned before, for some Chelsea boots, zippers may also be added in place of elastic sides. Even with all this variation, for Chelsea boots, less is more. Keep it minimal, and you’re going to be that much closer to an authentic Chelsea boot.

Zip Ankle Boots

are named for the side or back zips that appear in place of elastic to help keep the boots on your feet. It’s a less classic option, but equally versatile for a pair of Chelsea boots. While zippers help with fit and flexibility, these boots are technically not a true Chelsea boot, at least to menswear purists. But it’s not wrong to kick around in a pair either, plenty of times they offer a cleaner shape than traditional Chelseas.


Is the technical term for the “wingtips” on your wingtips. The perforated designs are all a matter of personal preference, but they’re not necessarily ugly—just not as popular as the smooth silhouettes you see on stylish dudes all over the place these days.

Leather Boots Are Easier To Care For Than Suede, But Suede Looks More Luxe

This is a decision that will affect how your Chelsea boots wear over time (and where you can wear them). Traditional leather is great for its versatility and durability, but suede is going to look more luxe at the cost of requiring more upkeep. Basically, you can wear leather in far more weather conditions than suede, and that goes for any type of shoe—not just Chelsea boots. Either way, you’ll want to make sure to treat either material before wearing your boots; just make sure you have a solid brush and cleaner if you opt for suede—you’ll be investing time in maintenance.

When It Comes To Design, Less Is More

The beauty of a Chelsea boot is it’s simplicity. From its lack of laces to the minimized shape, the boot has lasted primarily because, well, it’s easy to wear time and again. One of the worst mistakes you can make is copping Chelsea boots with crazy detailing like broguing on the toe, or extraneous details in the body of the boot. Don’t over complicate it. Everyone from David Beckham to Kanye West has stepped out in Chelsea boots, and the unifying factor is their commitment to a simple, sleek design. We’re not saying that a little flair is a bad thing, and some classic styles include brogued toes or bright soles, but when it comes to trend-proof boots, simpler is always better.

You Really Get What You Pay For

Sure, this is true for a lot of clothing, but with Chelsea boots this is even more important. Less-expensive sole alternatives like cheap rubber, or poorly made elastic panels (or lack thereof) will deteriorate over time, and unlike the good stuff—a cobbler can’t bring them back to life. Lots of budget Chelseas hit the shelves with elastic that either stretches inconsistently, cheap zippers, or synthetic leathers. Before you buy, make sure to do your research. Go for trusted brands (Tricker’s, Crockett & Jones, and Church’s to name a few) rather than price tag. Take a look at those bargain versions in person and look for details like welting (a sign it can be resoled) and the quality of the material. Remember, just because something is expensive doesn’t mean it’s good.

Your Pants Should Cover The Top Of The Boots

Great, you scored your Chelsea boots. But do you have the right pants to pull them off? If you’re thinking of rocking them with shorts: Don’t. Chelsea boots simply don’t work with anything but pants. Unlike your other boots, Chelsea boots aren’t only streamlined, but they have a thinner boot neck than most other footwear, which means that they’re meant to be covered by your trousers.

While Menswear 1.0 dudes wore theirs with cuffed  selvedge denim or trousers without a break, the modern style is all about stacking. It may seem overcomplicated, but you want to drape your pants over the top of the boot, completely covering the neck. At the same time, your pants should still stack, sitting or standing, while covering over the boot. There are some exceptions to the rule, like noted style rebel Kanye West, who stacks his denim on top of his Bottega Veneta Chelseas, but like any rule—you gotta know it first before you break it.

Two easy ways to wear them: with denim or proper pants.

Street style anthologies would have you believing that a pair of Chelsea boots is meant for stacked light wash denim. But try putting on a pair the next time you’re wearing a suit. It’s not only that they look like dress shoes (with a boot shape), but they add a different flair that normal oxfords just don’t have. Similarly, they can dress up a casual look and replace a spot usually reserved for high top sneakers, or even Timbs.

Written By Greogory Babcock

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