26 Outstanding Men's Boots in Every Style Worth Trying

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ONCE THOSE cooler temps hit, it’s easy to feel despondent about the onslaught of rain, snow, mud and slush to come in the months ahead. But there is one silver lining—the seasonal change also signals the hunt for the best boots. Regardless of what style you're after, picking up a fresh pair might just be what gives you that much-needed boost to conquer even the most wretched of days.

As we inch closer to the wintry season, you may have found your current footwear rotation to be less than ample for battle–and with today’s extreme weather changes, the next blizzard could be around the corner, so it’s never too early to pick up a pair or two.

Or, on the other hand, perhaps you’ve already upgraded your best weather-braving boots and now you’re looking for more statement-making styles that can carry you from the office to the bar and from one wedding to the next—plus everything in between. Whatever your quest, we’ve rounded up some of the best men's boots in the biz, including the best rain, snow, and hiking boots, to the more fashionable desert, western and Chelsea boots.

Read more: Best Men's Shoes

#1320 Chelsea Boot

The Australian footwear brand has given new meaning to the Chelsea Boot. Unlike previous versions, the 1320 Blunnies combine comfort and durability with upgraded features. They're constructed with premium water-resistant leather, that includes a lined interior, comfy shock-absorbing footbed and a sturdy, grip-tastic outsole.

We love how they feel cushy around the clock. They slip on and off so easily and don't require any break-in period. No matter how rigorous your work lifestyle is, these bad boys are equipped to go through hell and back, while feeling like heaven. Also, they look great with a casual look, think—a flannel and denim trousers.

Read more: Best Chelsea Boots for Men

Marco Everyday Chelsea Boot

Meet your go-to, everyday shoe. It has all the trappings of a classic Chelsea boot (clean lines, elastic side panels, laceless design), and come water-resistant leather upper and cushioned memory foam insoles for extra arch support and cloud-like comfort, so you can wear them all day for any occasion.

We love the versatility of this shoe because there's no limits on where you can wear them. From the office to casual outings on the town, it can take you from day to night. Be it denim or chinos, any pant will fit nicely over the boot. Plus, they're super neat and chic—you'll score several compliments.

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Wyatt Chelsea Boots

True to form, the luxe French fashion house has adopted a classic footwear staple and given it the Saint Laurent treatment. The super-sleek boots in suede feature Cuban heels, elasticated side-gussets, hidden pull tabs and an almond-toe silhouette.

Classic 6-Inch Waterproof Boot

A literal icon, Timberland’s work boots are known as much for their swaggy style as they are for their built-tough practicality. The weather-proof qualities—like seam-sealed construction and down-free PrimaLoft insulation—make them a standout style.

Read more: Best Work Boots for Men

Moab 3 Mid Waterproof

For our nature lovers who enjoy hiking, here is your all-terrain outdoor companion—the Moab 3. Regardless of how many obstacles are along the way, you'd be in good hands because these boots know a thing or two about rugged trails. They have ankle support, maximum shock absorption and the best-in-class Vibram® TC5+ outsole for optimal traction and performance.

6-inch Classic Moc

Most of guys whose work outdoors and wear strapped belts lined with a bunch with tools would appreciate these boots. They have a roomy moc toe silhouette, weatherproof leather construction and the perfect wedge sole for standing on your feet all day. All that being said, you can bet they will last a lifetime. Also, who doesn't love the classic tan-gold taslan laces?

The Cartwright

Howdy cowboy. The Cartwright boot from Tecovas is ageless with its western flair, classic round toe and 1 ½” stacked angled heel. It has ultra-soft calfskin leather construction, rugged bovine lining, and quick-to-patina goat—so you'd be suited and booted for the ranch or the office.

Wallabee Boot Maple Suede

Clarks makes reliable, no-frills kicks that pull double duty on comfort and style. Take the classic Wallabee, which has a handsome maple suede finish, along with a moccasin construction and structural silhouette. Plus, their signature crepe sole will help your feet look and feel good for hours.

Mountain Pass

Made in Oregon, the Mountain Pass was created as a lighter weight alternative for your typical hiking boot. This new version from Danner displays a unified platform, combined with a low profile Vibram outsole. Plus, you can extend the life of your boot with the brand's recrafting services.

1460 Smooth Leather Lace Up Boots

Before Docs became popular amongst varying subcultures and fashion crowds, they were truly British work boots. The high-cut steel-toe stompers with slip-resistant soles are utilitarian by design, with the signature yellow stitching providing just enough attitude. And if you ever scruff them up, they can be buffed and polished for a fresh shine—unless the wear and tear has an artistic effect.

Tank Soft Toe Leather Work Boots

This budget work boot is an industrial construction site go-to. Its key features include Goodyear Welt construction for the utmost durability and soft nubuck leather that’s easy to break in. Over 9,500 five-star Amazon reviews trust this boot. With a loyal following that big, and a price that low, we can't help but recommend these as solid bang for your buck option.

Desert Boot Beeswax

We feel confident in saying: there's no shoe that quite compares to the Clarks Originals Desert Boot. A true original, the shoe burst onto the scene with its minimal, progressive style and sparked a universal footwear revolution. It's made with premium beeswax leather and finished with simple lace fastening.

Original Play Chelsea Boots

The favored Wellington-style brand of boots for celebs and royals alike, Hunter’s tall rain boots made from natural vulcanized rubber look just as good trudging through a British bog as they do on the city streets during annual fashion weeks.

Read more: Best Winter Boots for Men

The Original Duck Boot

Crafted in Maine with New England weather in mind—and designed by Mr. L.L. Bean himself—these rubber-bottom Bean Boots offer reliable traction and keep water at bay. Other notable features include a classic lace-up design for a secure fit, triple-needle stitching and a steel shank that adds support.

Read more: Best Duck Boots for Men

Chelsea Boot Black Antique

Black leather dress boots are undoubtedly one of the most versatile clothing pieces to make up your wardrobe. They’ll serve you well on the daily—be it the office or date night—and on occasions like weddings. Needless to say, the Chelsea Boot Troy Black Antique by Ace Marks is a worthwhile investment.

ØriginalGrand Chukka Boot

Part of Cole Haan’s ZERØGRAND collection that sees typical shoe styles afforded a modern edge, these city chukka boots with nubuck uppers and grippy TPU soles are wholly waterproof, making them an ideal alternative to more conventional-looking boots.

Read more: Best Dress Boots for Men

Diplomat Moc Toe Leather Boots

These moc toes (shoes with moccasin-style stitching on the top) are made via Goodyear welt construction, which is an industry term that basically means these boots will last you a lifetime. Dress them up or down, your choices are endless.

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Harvy

No matter the occasion, the Harvy chukka boot will fit the bill. This option has a supreme leather upper with an updated rubber sole and fully padded insole, which provides exceptional comfort for anything that calls for long-periods of being on your feet.

Camion Ankle Boots

The Sweden clothing retailer’s take on the traditional leather ankle-high boot include a square toe and chunky low block heel, which is ideal for a formal affair. Not only is its buffed calfskin leather is rich, but the inner side zip closure make slipping in and out of the pair an easy feat, while also adding a contemporary touch.

Classic Mini Boot

Oh yes, fight it all you want, but these booties—like most fashion trends from the aughts—are back, which means they’re likely here to stay. So, why not settle in for all the toasty feels? Like Tom Brady and Evan Mock, don’t be afraid to wear them out while running errands either.

Quest 4 GTX Backpacking Boot

Outdoor equipment company Salomon was founded in the alpine city of Annecy, placing it right at the center of the French Alps. With practical design advancements, like a shock-absorbing EnergyCell midsole and Contragrip rubber soles, you’re guaranteed triumphant treks in the most brutal weather conditions.

Read more: Best Hiking Boots

Iron Ranger Leather Boots

An all-American boots brand if ever there was one, Red Wing Shoes has supplied footwear for everyone including soldiers and miners. This round toe-cap shaped pair in leather incorporates brass speed hooks for super-quick lacing.

Icebreaker Cold Weather Boot

These tall, waterproof boots are made for winter. Rated for -75-degree weather, your feet will stay warm no matter what. And just in case you need more convincing, there's also an adjustable nylon collar and wool lining.

Read more: Best Snow Boots

Why Trust Us

At Men’s Health, our testing editors and writers always make sure to actually test and use the products ourselves before considering whether to include them. Therefore, rest assured that our product recommendations derive from first-hand experience, and you can read more about our testing process here.

In addition, we have a whole fashion closet in our NYC office dedicated to calling in, trying out, and selecting the best and newest menswear products. We put them on stylish, fit guys to hear their opinions and see how the items look on them before making our final decision. And as style editors, we constantly go into the fashion closet to test out the products.

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