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We don’t need to tell you that boots rule. It feels like a very natural assertion to make, given their inclination to durability, versatility and general badassery. From Dr Martens to Red Wings, the best boots for men have long provided guys a solid alternative to sneakers and loafers, especially when weather or conditions get tough and additional coverage or warmth is warranted.
We will readily admit, however, that there are about a gazillion diffrent styles of boot — each special in their own way — to remember, consider and tug on before heading out the door. Straightening out when to wear chukkas or Chelsea boots to work is a full-time job within itself. Are western boots and cowboy boots that different? (Answer: yes.) Which pairs are the best? It’s these questions and more that have prompted us 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 diffrent types of boots for the fellas, from rugged work boots to weatherproof rain boots to sleek dress boots, along with our top picks from trusted brands. 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.
Boot Styles You Should Know
The Best Boots for Men
Chelsea Boots
Key Features: Vented sides, pull tabs
Name a boot more versatile than the Chelsea. We’ll wait. There is a side-paneled style for virtually every occasion imaginable, from lugged Blundstones to r/malefashionadvice-approved YSL Wyatts, each with their own proclivities and all united by a comfort-meets-sophistication vibe. Make sure you have a pair (or four) on you at all times.
The Best Chelsea Boots for Men, From Backyard to Black Tie
Name a more versatile boot than the classic Chelsea. We’ll wait.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.
Versatile, Timeless and Sturdy as Hell: The Best Chukka Boots for Men in 2023
Dust off those desert bootsWork 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.
The Best Rain Boots for Men Are Splash-Proof Perfection
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