How to Wear Chelsea Boots (and What to Look For When You Buy Them) (2023)

The best part about laces is that even if your shoes don't fit perfectly, they can be tweaked to until your kicks are somewhat comfortable, but when you're buying Chelsea boots, you'll likely be wishing you had the wiggle room laces provide. 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.

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.

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 coppingChelsea 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.

While you can buy bargain brands at the grocery store, you may want to consider saving up the extra dough when it comes to your Chelsea boots. We understand that dropping several hundred dollars isn't a realistic ask for those who want to cop the style, but what you add in the price, the more last you'll get off the boot.

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.

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 KanyeWest, whostacks his denim on topof hisBottegaVenetaChelseas, but like any rule—you gotta know it first before you break it.

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 evenTimbs.