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The 7 Best Chelsea Boots For Men To Slip On in 2021

Man wearing denim jeans and chelsea boots on the streets.

You wouldn’t know it by looking at them, but of all the best boots on the market, Chelsea boots might just have an interesting backstory. After being invented for Queen Victoria (yes, they were originally designed for women, but that doesn’t make them any less unisex now), Chelsea boots surged in popularity until the beginning of WWI, when they fell out of fashion. That is, until the mods brought them back in the ‘50s and ‘60s in the Chelsea district of London — thus the name they go by today.

In the decades since, men’s Chelsea boots have waxed and waned in popularity. But regardless of where they stand in terms of trends, there’s no denying that Chelsea boots have earned their place as a footwear style essential. Which brings us to the question we’re here to answer: What are the best Chelsea boots to buy right now?

Unfortunately, like anything in style, we can’t just pick a single pair, call ‘em the best Chelsea boots, and be done with it. No two men’s personal styles are created equal, so there is no end-all-be-all answer. What we can do, though, is give you some things to be aware of when looking for your “best Chelsea boots.” First off, look for boots that hit at the ankle for optimal support and versatility. They should also be made from two pieces of shaped leather — one at the heel and one covering the arch and toes — connected by an elastic bit on the sides. Last up, pay close attention to the shape of the toe. You’re looking for the perfect middle ground between sharp and blunted, ideally a kind of rounded point. This will help them toe the line (pun intended) between formal and casual, allowing you to dress your best Chelsea boots up with a suit, or keep it casual with a nice pair of dark-wash denim jeans.

Need more help? We’ve got your back with what we consider seven of the best Chelsea boots on the market at this very moment.

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Common Projects Sand Suede Chelsea Boots

Common Projects Sand Suede Chelsea Boot on a plain background.

Common Projects’ mastery of everyday essential footwear is unrivaled and that applies to their version of the Chelsea boot. Available in a tan suede that’s become basically synonymous with the best Chelsea boots in recent years, they feature a crepe sole that’ll keep you comfortable wherever the night takes you.

Saint Laurent Wyatt 40 Chelsea Boot

Black Saint Laurent Wyatt 40 Chelsea Boot on a white background.

Since the day Saint Laurent crafted their first Chelsea boot, the brand has ruled the genre. And the Wyatt is its flagship shoe. We consider it the platonic ideal of Chelsea boots. With a slight heel, sleek leather upper, and perfectly pointed toe, it gives off perfect rocker vibes fit for both celebrities and style-minded regular folks alike.

Dr. Martens Vegan 2976 Felix Chelsea Boots

Dr. Martens Vegan 2976 Felix Chelsea Boot on a plain background.

Doc Martens may be known for their iconic lace-ups, but their Chelsea boot is just as solid — and infused with that same punk rock spirit. Plus, you can get them in vegan leather, so you don’t have to worry as much about the ethics of it all.

Astorflex Bitflex Chelsea Boot

Astorflex Bitflex Chelsea Boot on a white background.

One of the reasons we’re into these Astorflex Chelsea boots is that they’re eco-consciously crafted in Italy using all-natural dyes by a family that’s been doing just that for six generations. The other reason is that they’re just really nice boots.

The Row Burnished Leather Chelsea Boots

The Row Burnished Leather Chelsea Boot on a plain background.

You may be surprised to see a pair on this list from The Row, the fashion brand founded by Mary-Kate and Ashley Olsen, but these Chelsea boots really are worth your attention. The thick elastic bands give a modern twist to this classic style and the burgundy calfskin leather, well, that’s just really nice to look at.

Church’s Houston Chelsea Boots

Church’s Houston Chelsea Boot on a white background.

We can’t make a list of the best Chelsea boots without including one of the British brands that no doubt fashioned some of the very boots that brought them back to popularity in the ‘60s. Church’s has been crafting quality footwear since the 1800s, and their Houston boot is a testament to the mastery they’ve achieved over the centuries.

Blundstone Original Suede Boots

Blundstone Original Suede Boot on a white background.

Rugged is an understatement when you’re talking about Blundstone boots. Take these water-resistant waxed suede Chelsea boots: they not only look great, but they can take on literally anything you throw at them, from hiking the backcountry to stomping the city streets.

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