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Casual Men’s Boots Are Our Winter 2022 Staple — SPY the Season’s Best Looks

Another season, another excuse opportunity to buy new footwear. But what to buy? You can never go wrong with a pair of casual boots for men. With so many workplaces relaxing their dress code and tons of people still working from home, at least part-time, it makes sense to buy boots that have a relaxed style that easily fit in with what you’re already wearing.

In our efforts to connect SPY readers with the best boots, we’ve already covered the season’s best Chelsea, Cowboy, and combat boots. For each of those styles, there are casual, work and going-out versions. In this piece, we’re concentrating solely (pardon the pun) on the best casual boots men can wear right now.

Casual boots can encompass a wide range of styles, and some of our favorite boot brands — Dr. Martens, Hunter, Cole Haan, Thursday Boot Co., Wolverine — make some excellent casual boots for men.

What Is a Casual Boot?

A lot of casual boots for men are based on the classic men’s heavy-duty work boot. We’re talking a thick rubber outsole, laces up over the ankle, a leather construction, a padded throat and a very plain silhouette. The modern casual boot for guys can come in suede, nubuck, Hoween leather,  and even vegan materials. While some may lace up, they’re at once a tad more refined and a tad more laidback than the classic work boot. You can find casual boots that have a cap-toe, or a sneaker-type outsole and even faux laces.

In addition, many casual men’s boots are basically souped-up versions of the loafer. Think ultra-cozy Ugg boots that are perfect for quick errands or lazy weekends at home.

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To help you find the perfect pair, we’ve collected the best men’s casual boots at varying price points. We think our selections do a pretty nifty job of combining boot badassery and slipper-type comfort.


1. Thursday Boots Captain Lace-Up


These leather boots have a touch of rockabilly vibe, so go ahead and peg your jeans (if you want to) when you lace them up. These casual boots have tonal topstitching and a cap toe. This featured pair is in Arizona Adobe, a burnished brown shade that has a slightly aged patina. Built for durability, style, and comfort, these leather boots have features that you’ll only find in pricier pairs of kicks. We’re talking featurs like cork bed midsoles that mold themselves to your feet, Poron Antimicrobial Shock Absorbing Insoles, Goodyear welt construction, steel shanks, and custom eyelets.

In 2021, we named Thursday Boots the best men’s boot brand of the year, and the company’s products make frequent appearances in our style guides because of their quality, price and stylish designs. On top of that, Thursday Boots are made by artisans from around the world who are always paid a fair wage.

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Courtesy of Amazon

2. L.L.Bean Classic Duck Boots

When selecting the best casual boots for Winter 2022, we just had to include the classic duck boots from L.L.Bean! Every fall and winter we collect the best men’s duck boots of the season for our readers, but nothing tops the original, which has gone pretty much unchanged for 100 years. This is a great all-weather boot for guys who aren’t afraid of a little mud and rain.

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Courtesy of L.L.Bean


3. Kenneth Cole The Life-Lite Hiker Sneaker


The very word “casual” denotes a relaxed attitude, and these sneaky hybrid sneakers are totally kickback casuall. This featherweight boot’s upper is styled like a hiking boot, complete with padded collar and laces. However, it rests on a sneaker bottom that has a shock-absorbent heel and cushiony padding. Try it with joggers or cords.

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Courtesy of Kenneth Cole

4. UGG Neumel Chukka Boot


Of course, when you do a roundup of the best casual boots for men, you have to include the chukka boot. This legendary boot, also known as the desert boot, came into being sometime around the early 1940s, and by the sixties, they were the popular boot to wear. They’ve never gone out of style, and UGG elevates this classic style by lining it with wool that’s been treated to look like shearling and the outer uses durable yet soft suede. These guys are so plush, you may never want to take them off.

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Courtesy of Nordstrom

5. Wolverine Blvd Cap-Toe Boot


Looking for a snazzy men’s casual boot that dresses up easily? Wolverine’s Blvd boot is it. The design is based on their classic 1000 Mile boot, with its premium leather upper and Goodyear welt. The stitched cap toe adds a little something extra to it, so if you decide to pair it with, say a pair of dress trousers, it will match perfectly. And this same boot is just as comfortable riding a motorcycle as it is strolling down a street.

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Courtesy of Wolverine

6. Dr. Martens 1460 Panel Leather Lace Up Boots


Every guy needs a pair of Dr. Martens in his wardrobe. The brand’s iconic combat boots are comfortable and have a timeless appeal that’s perfect for casual winter outfits. Heck, they’ve been worn by everyone from German housewives in the 40s to punk rockers in the 70s. The brand literally makes hundreds of styles for men, women, and kids. We picked this version of the 1460 lace-up boot because it’s a stylish combination of leather and breathable nylon. The tonal differences are eye-catching, and the boot comes with a waterproof and durable Goodyear welt.

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Courtesy of Dr Martens

7. Allen Edmonds Freeport Weatherproof Lug Boot


Handsome and rugged, Allen Edmonds moc-toe boot is impervious to bad weather. Handcrafted in Port Washington, Wisconsin, this casually cool boot has a thick yet lightweight lug sole, an inner waterproof membrane, and 360-degree waterproof welt construction that is sealed against rain, snow, mud, and muck. The outer is crafted from waterproofed Horween leather that is soft to the touch.

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Courtesy of Allen Edmonds

8. Cole Haan 4.ZEROGRAND Explore Boots

Cole Haan’s excellent 4. ZEROGRAND line of modern boots is stylish, rugged and unlike anything else for sale in 2022. We got the chance to test out the brand’s first urban hiking boots back in 2020, and we’re still in love with the look and feel of these boots.

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Courtesy of Cole Haan

9. Hunter Original Chelsea Boots


In recent years, Hunter’s Original Chelsea Boots have exploded in popularity, so much so that certain colors are hard to find as the winter comes to a close. These are truly iconic rain boots for the modern man (or woman!), and an easy choice when selecting the best casual boots of the season.

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Courtesy of Zappos

10. Timberland Port Union Waterproof Boot


Timberlands are a sturdy bunch; these boots have trampled snow for generations. The Port Union style is everything you want in a wintry weather boot; waterproof, durable with an outsole that grips everything. The upper uses sleek, flexible Sensorflex leather and lined with the brand’s own TimberDry membrane to keep feet dry even when the puddle goes over your ankle.

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Courtesy of Nordstrom

11. Dr. Martens Vegan 101 Felix Ankle Boots


Did you know that Kanye West, Pope John Paul II and Cardi B are among the legion of famous people who own Docs? Well, if you’re ever on Jeopardy, this knowledge could help you out. Seriously, they’ve been a hit since they first hit the streets in the 40s, and while they’re best known for their leather boots, their vegan boots also have a huge fan base. The Felix is one of their shorter lace-up boots and has the same air-cushioned soles as the leather ones. Made from a synthetic material known as the Felix Rub-Off, the entire boot is vegan-friendly.

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Courtesy of Dr. Martens

12. L.L.Bean X Todd Snyder Bean Boot in Heritage Plaid


L.L. Bean and Todd Snyder have been dropping collabs this fall, and we hope that they don’t stop working together. While we did cover this boot in the latest launch, it’s so cool that we had to include it in this roundup of the best casual boots for men. Snyder used Bean’s handsome heritage buffalo check to highlight their duck boot’s shaft. It sits atop the classic duck boot and underneath the rubber top is the brand’s iconic tire tread outer sole.

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Courtesy of Todd Snyder

13. Roots Tobermory Chelsea Boot


No longer do you have to forsake style for comfort when the temps dip into the negatives. Canada-based Roots has been making handsomely styled (and warm) clothing for those living up north for years. Their Chelsea boot has a waterproof waxy nubuck leather outer and has a sherpa lining. They add more comfort by using Ortholite Eco-Hybrid insoles, so if you’re one of those people who love to wander around during a snowfall, these are your best friends.

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Courtesy of Roots

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