The Best Boots for Men, From Chelsea to Chukka and Beyond

Boots were made for walking. Ask anyone.

October 27, 2023 12:57 pm
a collage of boots on a brown background
The best boots for men make every day a bit better.
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We don’t need to tell you that boots rule — that feels like a very normal assertion to make, and to understand. From Dr Martens to Red Wings, the best boots for men have long provided men a solid alternative to sneakers and loafers, especially when weather or conditions get tough.

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We will readily admit, however, that there are about a gazillion diffrent styles — each special in their own way — to remember, consider and wear. Straightening out when to wear your chukkas and when to bust out the Chelseas is basically a full-time job. Which is why we’re here to offer our services and expertise, with a handy guide to all the boots styles you should know…and potentially own.

Below, we’ve outlined seven iconic silos of the best boots for men, from rugged work boots to weatherproof rain boots to sleek dress boots, along with top picks from brands ranging from Todd Snyder to Our Legacy. Each is dependable and good-looking, and every last one should serve you for years to come. Below, the best boots for men, from chukkas to Chelseas.

The Best Boots for Men

Chelsea Boots

Key Features: Vented sides, pull tabs

Name a boot more versatile than the Chelsea. We’ll wait. The side-paneled style is made in virtually every style imaginable, from lugged Blundstones to r/MFA-approved YSL Wyatts, each with their own proclivities and all joined by a totally badass vibe. Make sure you have a pair (or four) on you at all times.

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Dress Boots

Key Features: premium materials, slim-cut finish

Wedding on the docket? Speaking at a convention? Or maybe you’re just Del Water Gap and need a pair of kicks to match your Thom Browne shorts-suit. Skip the brogues and try out a snazzy dress shoe out instead — a sleek pair of leather or suede boots will take that two-piece to a whole other level.

Chukka Boots

Key Features: low-profile cut, crepe outsole

Chukka, desert boot; call it what you will, but the iconic style remains one of the top boots around when it comes to versatility and ease of wear. You can never go wrong with a classic Clarks crepe-soled style, but there are all sorts of opportunities to get freaky with, thanks to Japanese imports and modern Americana alike.

Work Boots

Key Features: premium leather or suede, easy-on lacing system

By far the broadest category of this list, work boots range from buckled engineer boots to hardwearing Red Wings to suede styles that could easily be confused for dress boots. The connecting thread? Work boots are made to get the job done, last decades and generally help you conquer whatever your day throws at you.

Hiking Boots

Key Features: treaded sole, abrasion-resistance, ankle support

Long gone are the days when hiking boots were just for geriatrics and obsessives. The advent of GORP and the realization that “hey, these are pretty comfy!” have left everyday guys more familiar with the Danners and Merrells of the world than ever before. This is a decidedly good thing — just make sure you buy a pair that you can actually hike in (read: lugged or treaded outsole for serious grip and an ankle support system for treacherous trails).

Cowboy Boots

Key Features: sturdy heel, pointed toe

Yeehaw! Westernwear is back, and so are iconic cowboy styles. While you might not be spurring on stallions or manhandling bales of hay, wrangling up a cowboy boot should be priority numero uno this season. Try classic styles from heritage labels like Lucchese, or walk on the wild side in some designed digs. We won’t judge.

Rain Boots

Key Features: water-repellant coating, rubber sole

Rain boots might not be the sexiest boot on this list, but with snow, slush and muck on the immediate horizon, it’s worth investing in a pair that’ll keep the dogs dry and barking. Consider the sole and coating first when purchasing a pair: rubber and super-repellant materials GORE-TEX (or nylon) make all the difference in torrential downpours.

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