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10 Stylish, Foul-Weather Boots That Will Last Forever

No one said you can't look great while fighting the elements.

It's officially that grim time of year. The fun part of winter is ancient history, football season is basically over (just one more game!), and you're starting to get very, very tired of wearing that same old winter coat day in and day out. Worst of all: between the hazy-shade-of-right-now and the sweet-warmth-of-spring are two gnarly months in which the ground is guaranteed to be covered in a nasty, slushy cocktail of snow and salt.

The good news is that your trusty foul-weather boots have come a long way in recent years. Gone are the days in which you had to dress like a card-carrying member of "Duck Dynasty" every time the weather turned ugly. Today's foul-weather shit-kickers offer not only the best warmth, waterproof features, and rugged tread, but they also look pretty snazzy with a suit. Bonus: They're pretty much guaranteed to last you forever.

As you stare down the worst stretch of winter, we've handpicked the best stylish boots that will help you trudge through it. Once you've raised your boot game, don't miss our Must-Have Blazers.

The Best Refined Hiking Boot

$360; Buy now at

Leave it to the folks at Danner, based in Portland, Oregon, to create what is essentially the perfect hiking boot. The Mountain Pass Waterproof model comes with a rugged and refreshingly handsome styling (ie. no goofy, oversized tread), and it'll stand up to the toughest of terrains.

The Best Chelsea Boot

$250; Buy now at

Suffice it to say, we're currently living in the era of the Chelsea boot, when there's nothing more fashionable than sliding on a pair of these bad boys underneath a great suit. (For the record, we're all for it.) The Warren Waterproof Chelsea from Cole Haan is super light and comfortable, with a tight, streamlined look.

The Best Pound-The-Pavement Boot

$190; Buy now at

If you really want to kick a snowstorm right in the ass, pick up a pair of these Chestnut Ridge Waterproof Insulated boots from Timberland. They're all leather, thermoplastic rubber, and testosterone—and, yes, they will keep your feet warm and protected through the iciest rings of hell.

The Best Rain Boot

$225; Buy now at

Yes, when it rains, it pours. But when it pours, be smart and protect yourself with these handcrafted Balmoral boots from Hunter.

The Best Sneaker Boot

$275; Buy now at nordstrom

There are a lot of hybrids we don't approve of: electric bikes (are you seriously too lazy to pedal?), tuxedo tees (OK, maybe that's not a hybrid), and puggles. (OK, just kidding.) But the newfangled "sneaker boot"—the comfort and styling of a sneaker combined with the rugged protection of a boot? We're all in, especially with this Holliston Mid Top Waterproof Boot.

The Best Motorcycle Boot

$498; Buy now at

Want to look like Marlon Brando in his prime? You can! Well, at least your lower half can. Just buy this pair of classic engineer boots from Frye.

The Best Chukka Boot

$160; Buy now at

Meet Clark's Chilver Hi GTX Chukka, perhaps the single greatest boot on the market for any casual get-up. Pair it with jeans, slacks, even a suit. (Just don't wear with shorts.)

The Best Snow Boot

$150; Buy now at

The 1964 Premium T snow boots from Sorel are ideal for any heavy snowfall: the vulcanized rubber will stomp through anything and the lining will keep your feet nice and toasty.

The Best Side-Zip Boot

$210; Buy now at shop.nordstrom

Admit it: this Blondo Valerio boot is so damn stylish you didn't even know it was waterproof.

The Best Comfort Boot

$250; Buy now at

The Woolrich Puritan Path Leather Waterproof Boot is a terrific everyday boot. It's got a comfortable wool lining, a fashionable heel, and it pairs with just about everything.


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