How to Wear Chelsea Boots (and What to Look For When You Buy Them)

The Chelsea boot isn't just perfect in its simplicty, but a must have for your wardrobe.

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We understand guys have questions about what to wear (and how to wear) their favorite pieces.  Stick with us all this week to get advice on how to look good, stay fresh, and even score a date. This is Complex Style's "How To" Week.

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. 

But considering that this silhouette hasn't seen this much play since the Beatles and The Rolling Stones were on the radio, guys have been wondering how to add this '60s staple into their modern-day wardrobes. Fear not, you don't have to dress like they did 50 years ago in order to pull this off (unless you're Hedi Slimane). Sure, it was one of the biggest trends of 2014, but we've broken down what you need to know and look for when you're wearing your Chelseas. This is How to Wear Chelsea Boots

They should fit snug, but not tight.

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Learn the different styles of boots out there.

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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 are similar 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.


Broguing 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.

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When it comes to design, less is more.

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You really get what you pay for.

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Your pants should cover the top of the boots.

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

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