15 Best Chelsea Boots for Men in 2025 That’ll Never Go Out of Style

The best Chelsea boots for men are trend-proof in a way that’ll make you breathe a sigh of relief. Especially right now, when menswear feels like a WWE Royal Rumble, where anything goes and trends pile up like bodies in and out of the ring. But there, floating confidently above everything, is the trustworthy Chelsea boot.

If we had to make an educated guess as to why the Chelsea boot has stuck around for so long? Good design is good design. The slip-on simplicity, the sharp silhouette, the unadorned, uncomplicated details—the pared-back design makes it highly adaptable to any wardrobe and occasion, trends be damned. So don’t be ashamed to cash in on a fleeting fad, but when it comes time for you to do some spring cleaning, we’d advise against letting go of a pair of Chelseas.

We’ve rounded up 15 of the best Chelsea boots out there, from hardwearing stompers to exquisite stunners, under-$200 steals to $1,500 beauties. Finding the perfect pair can be hard—but pulling them on? Easy.

The Best Men’s Chelsea Boots, According to GQ

The Best Chelsea Boots Overall

R.M. Williams Heritage Craftsman Leather Chelsea Boots

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The Best Budget Chelsea Boots

Beckett Simonon Bolton Chelsea Boots

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The Best All-Weather Chelsea Boots

Blundstone Classic 500 Chelsea Boot

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The Best Designer Chelsea Boots

Saint Laurent Wyatt Chelsea Boot

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The Best Ultra-Comfortable Chelsea Boots

Astorflex Bitflex Chelsea Boot

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Best Chelsea Boots Overall: R.M. Williams Heritage Craftsman Leather Chelsea Boots

Ask us what Chelsea boot you should get, regardless of price, and we’ll point to the R.M. Williams Turnout boot, because it does so many things right that the competition can’t. Off the bat, it’s a real stunner. The silhouette is sleek and chiseled, timeless and fashion forward. The leather is perfectly suited for a shine and polish to attend any black tie event, but takes on a handsome patina when worn hard. Plus, the quality is fantastic. The wholecut leather uppers are shaped as a single piece of cowhide rather than several panels stitched together, resulting in a shoe that’s as pretty as it is durable. With Goodyear-welted construction for easy peasy resoling, you’ll have these Aussie-born boots for well over a decade.

How does a boot originally built for Down Under cowboys manage to be the best-looking dress boot and hardest-wearing boot at the same time? Hard to say. The only drawback of the R.M. Williams Heritage Craftsman Chelsea is the price. But considering everything it can do—and how long it’ll last—the math makes sense.

Best Budget Chelsea Boots: Beckett Simonon Bolton Chelsea Boots

For the budget conscious/the dude looking for his first pair of “nice” Chelsea boots, my answer is easy: Beckett Simonon. Menswear bros might scoff at a web-only DTC clothing brand, but unlike the other brands with infinite marketing budgets looking to “disrupt the entire industry”, Beckett Simonon seems content with making great shoes at a great price, without all the soulless millennial pandering. The Bolton, a slick sleek, true-to-form  Chelsea boot, is just the poster child for the brand’s modus operandi. It uses full-grain Italian calfskin, which is lined with Vachetta leather, stitched by master shoemakers in Columbia using a Blake stitch construction.