Best Men’s Boots 2020

The Best Men’s Boots for Work, Play — And Everything Else!

When fall and winter weather rolls in, he who has the best boots wins. Whether you’re working all day on your feet, navigating a foul-weather commute, or having fun in the great outdoors, the right footwear can make the difference between a great day and a miserable one. (Just ask anyone who’s ever spent the day in soggy socks.) 

There are as many kinds of boots as there are reasons you need them, but a few basic truths apply:

Boot-Shopping Tips for Men

Check the product description for water resistance or waterproofing. While all boots are made to withstand a bit of weather, they’re not all equally effective at keeping out moisture. Depending on your needs, you may not need a boot that’s technically waterproof, but we recommend hitting fashion boots with a waterproofing spray before wearing. It’ll add an extra layer of protection, and help your new boots last longer, too.  

Don’t forget the socks! This may seem obvious, but you wouldn’t be the first guy to pick up a great pair of boots, only to realize your everyday socks just don’t work with them. Even if your job doesn’t keep you on your feet, we recommend a good work sock under most types of boots for cushioning, moisture-wicking and durability.

Size up, not down. Boots are, by definition, chilly-weather shoes — so leaving room for those thick, comfy socks can only be a good thing. 

To bring you one step closer to your ideal pair, we’ve scanned our inventory and rounded up the absolute best of this year’s styles in every type of boot.

Best for Style: Skechers Blain-Orsen Dress Boot
Skechers Blain-Orsen Men's Comfort Boot

Rain and light snow are no threat to your best outfits with the right pair of boots  in your closet. The Blain Orsen from Skechers  complements your nicer casual wear with classic lines, simple styling, and attractive top-stitched details. But make no mistake, with a  quality leather upper and  high-traction outsole, this pair is definitely weather-worthy. 

Best for Rain: Sperry Avenue Duck Boot

When it’s pouring outside, nothing beats a duck boot (except maybe staying indoors). We love the way this Sperry classic delivers warmth and waterproofing without a lot of bulk or weight. Specially sealed seams prevent leaks in the upper, while famous Sperry Wave-Siping™ texture in the rubber outsole funnels water away from the foot for a no-slip grip. 

Best for Snow: Totes Stadium Snow Boot
Totes Stadium Men's Weather Boot
Good news: you don’t have to clomp around like a bundled-up kid to score serious warmth and waterproofing on snowy days. This sleek boot’s deceptively simple appearance hides a multitude of high-performance features, like a lightweight hybrid upper (made from faux leather and microfiber) and a cozy-but-concealed faux fur lining. As the name hints, these are a winning choice if you’re outside watching a game. Let it snow! 

Best All-Purpose: Caterpillar Deplete Waterproof Boot
If you’re only going to own one pair of boots, we’d push for the Caterpillar. Think of it as the perfect no-frills, mid-height, waterproof boot; a workhorse that’ll keep feet dry and comfortable no matter what Mother Nature dishes out. With a leather upper, specially cushioned EASE footbed, lightweight EVA midsole, and rugged traction outsole, this pair checks every box for comfort and performance. (Not to mention classic good looks!)

Best Hiker: Timberland Mt. Maddsen Hiking Boot
main product photo
When you’re out on the trail, performance takes on a whole new meaning. Do your feet a favor by choosing a pair specially made for the active outdoors. The Mt. Maddsen from Timberland does the job with a waterproof, full-grain leather upper, and special Timber-Dry interior membrane for serious water protection. Looks just a good out around town, and with special anti-fatigue cushioning technology in the insole, who knows how far you’ll go? 

Best Pro Work Boot: Timberland Pro Titan
Timberland Pro Titan 6 Inch Men's Safety Toe Boot
Footwear on the job is serious business, and Timberland meets the challenge on every level. Safety comes first with tough steel toes, electrical hazard protection, and a slip-resistant rubber outsole. Comfort comes next with a rugged-but-malleable leather upper, thick padded tongue and collar, and cushioned insole. Plus these boots look great — and will keep looking great thanks to an oil-resistant finish. 

Best for Sportsmen: Itasca Camo Sloped Neoprene Boot
If you see winter as one big outdoor adventure, you’re gonna need boots that can keep up. Nothing gets past an ultra-warm, high-rise neoprene upper, so this pair is totally sloppy-weather ready. Plus, the thick rubber outsole climbs high on the ankle to block water completely, even if you’re walking right through it. Simple, pull-on construction is one more guarantee of serious waterproofing, and thanks to a durable pull-tab, getting these bad boys on and off is a snap. 

From fashion to function, be prepared with a boot collection that’s as ready as you are to handle whatever the day brings.