The Best Chelsea Boots for Effortlessly Stylish Men in 2023

By Beau Hayhoe  |  Updated October 13, 2022

The Best Chelsea Boots for Effortlessly Stylish Men in 2023
Courtesy of Astorflex

When you think you’ve got a solid grip on your footwear rotation, perhaps filled with pairs you love to wear, it can be fun – yes, fun! – to throw a little something different in the mix. This is where the Chelsea boot comes into play.

While we’re willing to bet you’ve got rugged work boots, classic chukka boots and perhaps some lace-up captoe or wingtip boots, the best men’s Chelsea boots take your footwear collection to another level. 

And if you’re like us, it seems there’s never really a bad time to break out some Chelsea boots (except the high heat of summer, when it’s a better bet to wear something like casual loafers). Particularly during the fall and winter, Chelsea boots amp things up a bit – they signal refinement and sleek style – the sort of dressy appeal that can be worn with tailored trousers or chinos.

Yet, the best Chelsea boots are also able to be worn with tailored blue jeans and an Oxford shirt for business casual looks. While we’d advise against pairing Chelsea boots with, say, lounge pants, plenty of casual, biz casual and tailored looks will look even better with the right set. The elastic side design makes Chelsea boots easy to pull on and even easier to wear, and materials like suede and rich leather give you options. 

For instance, you can pair shades of brown with navy blue chinos or light wash jeans, and common colors like black Chelsea boots wear perfectly with light grey denim, olive chinos or – of course, black jeans. They add a dash of on-trend edge, they signify you mean business and hey, the best Chelsea boots are just downright cool. These are the pairs we’ve got our eyes on right now.

For more options, head over to our comprehensive guide to the best boots for men.

FRYE Tyler Chelsea Boots


Some Chelsea boots are every bit as streamlined and sleek as your go-to dress shoes, and FRYE certainly hits the mark with the Tyler Chelsea Boots.

For starters, the premium black leather upper gives them a bit of rock star sheen, especially when worn with black jeans or even a navy suit (yes, navy and black work well together – James Bond would approve).

The use of rubber in the leather outsole gives them a bit of hard-wearing sturdiness, while the leather-lined footbed will mold to your foot over time.

Astorflex Bitflex Chelsea Boots


Not every pair of Chelsea boots is as dressy as those black leather FRYE boots we just discussed. In fact, these handsome suede Chelsea boots – made by family-owned Astorflex and sold by rugged style purveyors Huckberry – definitely lean more casual.

It comes down to the springy, soft crepe rubber sole for plenty of comfort and laidback style, along with the all-natural aged leather upper. Team these with your favorite pair of faded jeans and a classic henley to nail a casual, everyday look.

New Republic Sonoma Suede Chelsea Boots


It’s hard to find a better value on the market for Chelsea boots than New Republic’s fan favorite Sonoma Boots. They retail for under $100 when on sale, with some serious style points that make them look like a much more expensive pair of boots.

The use of tan suede is eye-catching and stylish, especially when paired with deep navy blue jeans or olive chinos, while they sit atop a comfortable crepe rubber sole for all-day comfort.

Blundstone #510 Boots


Blundstone boots are legendary in our book, and if ever you’ve worn these ridiculously dependable pull-on boots to tackle yard work or take on a rugged fall cabin getaway, you know the drill.

The Australian company has made these boots for decades, using tough yet supple leather and a slip-resistant outsole to provide traction and reliable performance seemingly no matter the weather. Get a no-frills black pair and wear them to handle chores – then, clean ‘em up and wear them to a dive bar or rock concert, because they can nearly do it all.

Beckett Simonon Bolton Chelsea Boots


The Chelsea boot is a statement-making set of footwear, and that’s certainly true when worn alongside your best navy or charcoal suit.

Beckett Simonon’s Bolton Chelsea Boots are made to rise to the occasion, with Italian leather and an expertly crafted design that’s all about tailored refinement. Specifically, they’ve honed in on a tapered design that makes them supremely well-suited to, yes, dress in your Sunday best through fall and winter.

Rhodes Footwear Blake Boots


The latest and greatest from Huckberry’s own Rhodes Footwear blends a few key components: The sleek and easy-to-wear styling potential of a Chelsea boot, plus the rugged dependability of a work boot.

They’ve reinforced these boots with tough roughout leather made to withstand abrasion and get better with age. And for good measure, they sit atop a lightweight outsole that delivers some serious spring in your step. If you want a pair of Chelsea boots to wear with jeans, get this pair ASAP.

Taylor Stitch Ranch Boots


Taylor Stitch hits the right balance between road-ready, hard-wearing and yet remarkably stylish with the handsome Ranch Boots. Think of them like a hybrid between a dressy Chelsea boot and a moto boot, with resoleable construction – after years of wear – and heavy-duty elastic detailing.

These boots are also finished with a tough-as-nails Vibram mini-lug sole – you won’t lose your grip on slippery city streets. The Saddle Tan leather will also only get better the more you wear this pair of the best Chelsea boots, and it’s helpful that they look right at home with navy Taylor Stitch chinos.

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