26 Outstanding Men's Boots in Every Style Worth Trying
26 Outstanding Men's Boots in Every Style Worth Trying
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, copping a fresh pair might just be what gives you that much-needed boost to conquer even the most wretched of days.
And even though we're only in the early weeks of Fall, 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.
The Australian footwear brand upgrades its Original #500 design to make it even more all-weather worthy. The souped-up Blunnies in premium water-resistant leather include a lined interior, comfy shock-absorbing footbed and a sturdy, grip-tastic outsole.
Meet your go-to, everyday shoe. It has all the trappings of a classic Chelsea boot (clean lines, elastic slides, laceless design), and come with 2022 features like a soft suede lining and cushioned footbed for extra arch support and comfort, so you can wear them all day at the office.
Clarks makes reliable, no-frills kicks that pull double duty on comfort and style. Take this Chelsea boot, which has a handsome dark suede finish, along with a proprietary footbed that will help your feet look and feel good for hours.
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.
Robert Polished-Leather Chelsea Boots
The king of American glam adds a glossy touch to this pair of brown Chelsea boots crafted from calfskin leather. On top of the characteristic pull tabs and elastic-sided construction, these Robert boots boast lightweight rubber soles for next-level comfort.
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.
Astorflex, an Italian family-run business since the 19th century, produces eco-friendly footwear. These chukka boots are handcrafted from premium leather that’s been aged for 30 days in a combo of water, oak bark, and powdered mimosa. How fancy.
Plain Toe Chukka Boot
Say you’re not going on a hike, but rather traversing the urban jungle. A versatile chukka style is upscale enough to pair with a suit or just your casual weekend uniform, but will still protect you from rainy days. It has a rubber sole, waterproof leather, and a super-comfortable footbed.
Only with Nisolo is the Peru-Nashville pipeline a thing. The company’s shoes, including the Everyday Chukka, are handmade in the South American country with workers paid a living wage. It’s a real look-good, feel-good option.
Men's 6-inch Premium Waterproof Boots
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.
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.
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.
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.
Men's Diplomat Moc Toe Leather Boots
Thursday Boot Company
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.
Chunky combat boots will elevate any fit, so rock them with your favorite casual items, like jeans, T-shirts and a leather jacket. Camper’s nubuck leather combat boots with a stacked heel look extra cool in a military-inspired green.
Men's Original Tall Rain 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.
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.
Crafted in Maine with New England weather in mind—and designed by Mr. L.L. Bean himself—these rubber-bottom Bean Boots keep any water at bay and feature Thinsulate Insulation that’s built to beat the winter chill.
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.
Black leather lace-up 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. This pair by legendary British shoemakers Grenson is a worthwhile investment.
If you think that wool is just for cozy sweaters, think again. The Livingston Boot by Taft is made with winter-ready printed wool and a sharp Spanish leather wingtip accent. Plus if you wear down the sole (and we wouldn’t be surprised) the Blake-stitched constructions means you can easily replace them.
Lace-up Leather Boots
The Spanish clothing retailer’s take on the traditional leather lace-ups in brown include a rounded toe and steady rubber soles. The zip fastening on the sides make slipping in and out of the pair an easy feat, while it also adds a contemporary touch.
Dalton Wingtip Dress Boots
The small perforations on brogues, like these, were originally designed to speed up drying of the shoe’s upper in wet climes. Though they were once considered appropriate only for the outdoors, today they’re an ideal smart casual companion, with Allen Edmonds making a wonderful wingtip number.
Western Ankle Boots
If genuine cowboy boots are a little too daring for your taste—if they don’t intimidate you at all, we applaud you—then Italian luxury goods manufacturer Tod’s has a perfect interpretation of the iconic silhouette that should give you the confidence to strut your stuff.
There may not be much substance to take away from Kanye West these days, except perhaps a style tip or two when it comes to the way he tackles footwear—the rapper has donned really affordable yet equally stylish boots. And yes, the tire brand makes some durable footgear.
Men's Classic Mini Boots
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.
Men's Health's editors tested the best men's Chelsea boots, work boots, dress boots and beyond. Choose from some of the best boot brands including Timberland, Dr. Martens and more.