The Best Boots for Men Are the Obvious Solution to Your Footwear Indecisiveness

Now, more than ever, boots are on my mind. I say now specifically because, in this post-sneaker-loafer-dress shoe world, where labeling a trend as “micro” is generous, the best boots for men provide the sole alternative to low-profile footwear, especially when weather or conditions get tough and additional coverage is warranted.

For this reason, boots have found themselves as something of a great unifier, a footwear so versatile and durable that anyone, regardless of their personal background, style vibe or designerwear budget, can get behind.

Understatedly, this reputation is predicated on the fact that there are about a gazillion different styles of boots — each special in its own way — to consider, especially during the downright soggy nastiness of winter. Straightening out when to wear chukkas or Chelsea boots to work is a full-time job in itself. Are Western boots and cowboy boots that different? (Answer: yes.) Which pairs are the best for trudging through three-day-old snow?

It’s these questions and more that have prompted me to offer my services and expertise, with a handy guide to all the boot styles you should know…and potentially own.

From Dr Martens to Red Wings, I’ve outlined seven diffrent types of boots for virtually every demand — these range from rugged work boots to weatherproof rain boots to sleek dress boots — along with my top picks from the trusted brands out there, names like Wolverine and R.M. Williams. 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, By Category

• Editor Picks
• Winter Boots
• Work Boots
• Hiking Boots
• Chelsea Boots
• Zip Boots
• Dress Boots
• Chukka Boots

Winter Boots

Winter boots might not be the sexiest style on this list, but with snow, slush and muck unceasing for the immediate future, it’s worth investing in a pair that’ll keep the dogs dry and barking. These aren’t just glorified rain boots, or leather numbers with lugs — a proper winter boot is built with hyper-specific properties to counteract the worst of the season’s cold and snow. To that end, there’s much to consider when purchasing a pair: rubberized and super-repellent materials like Gore-Tex make all the difference in torrential storms, especially when combined with a higher silhouette, and a fleecy interior — shearling, sherpa, or wool — is mandatory in bitter conditions. Don’t forget about the outsole, either. Beefed-up, snow back-busting lugs make all the difference in icy conditions.

Work Boots

By far the broadest category of this list, work boots are more of an umbrella than a bucket. Styles vary greatly, from buckled engineer boots to hardwearing Red Wings to suede styles that could easily be confused for dress boots. The connecting thread? Beyond the technical aspects — the style typically features primo cushioning, a lockdown fit and a high-quality, super-grip sole unit — work boots are made to get the job done, last decades and generally help you conquer whatever your day throws at you, which makes them the perfect choice for any guy looking to invest in a single pair of shoes for…well, everything. Keep your eyes peeled for hallmarks of quality, features like Vibram soles, genuinely goodyear construction and handmade craftsmanship, and you’ll be hard-pressed to find a disappointing pair.

Hiking Boots

Long gone are the days when hiking boots were just for geriatrics and outdoor 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, which is a decidedly good thing, given that the style’s emphasis on cloud-like cushioning, ankle support and, increasingly, grade-A weather-resistant technology make them an excellent pick-up for anyone constantly on the move, whether that’s scrambling over cliffs or braving the urban jungle. 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).

Chelsea Boots

Name a boot more versatile than the Chelsea. We’ll wait. There is a side-paneled style for virtually every occasion imaginable — lugged leather Blundstones, r/malefashionadvice-approved YSL Wyatts, rocker-esque Kentons, even a Tabi-toed Margiela number. From gardening to Madison Square Garden-ing, Chelseas have their own distinctive proclivities and use cases, but the style is traditionally united by crispy leather or suede outer (I prefer the former) and a comfort-meets-sophistication vibe. Make sure you have a pair (or four) on you at all times.

Zip Boots

Zippers are to boots what leather jackets are to outerwear — an immediate, obvious telegraph of being chill like that. Increasingly, they’re also the footwear du jour for fashion’s biggest steppers, especially as modern labels (we’re looking at you, Our Legacy) have introduced sleek leather styles designed for the coolest among us and built to play nice with massive trousers and tiny tops. Squarer toes and side zips have become the desired hallmarks, but don’t shy away from a dressier situation, either, so long as you have the confidence to pull it off.

Dress Boots

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 derbies and try out a snazzy dress boot instead. A sleek pair of leather or suede boots will take that two-piece to a whole other level, especially styles that incorporate classic dress detailing like tasteful brogueing or a rakish cap toe. This is not to say that they can’t also do some heavy lifting — more modern options now often feature lugged outsoles and scratch-proof uppers.

Chukka Boots

Chukka, desert boot — call it what you will, but the iconic suede style (originally conceived of as militarywear) remains one of the top boots around when it comes to pure versatility and ease of wear. Throw them on with your work suit or a cooked pair of Levi’s, and the result is still the same: rugged charm that’s just formal enough to pass muster. 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 new Americana designs that mess around with leather uppers and modified sole units.