Casual Boots Are Our Winter 2022 Staple — These Are the Boots To Buy

best men's casual boots
Dr. Martens
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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 offices relaxing their dress code, and 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. We’ve covered Chelsea, Cowboy, and combat boots before. 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.

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.

We’ve picked 10 casual boots in varying price points that 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 find in pricier pairs. We’re talking items like cork bed midsoles that mold themselves to your feet, Poron Antimicrobial Shock Absorbing Insoles, Goodyear welt construction, steel shanks, and custom eyelets. We’ve used Thursday Boots in other roundups because they’re known for their incredible quality and integrity.  Thursday Boots (and shoes) are made by artisans from around the world and paid a fair wage.

Thursday Boots brown Captain lace up boots Courtesy of Amazon

Thursday Boots Captain Lace-Up


2. 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 brands iconic tire tread outer sole.

L.L.Bean-X-Todd-Snyder-Bean-Boot-In-Heritage-Plaid Courtesy of Todd Snyder

L.L.Bean X Todd Snyder Plaid Bean Boot


3. 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.

Roots-Tobermory-Chelsea-Boot Courtesy of Roots

Roots Tobermory Chelsea Boot


4. 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.

Wolverine-Blvd-Cap-Toe-Boot Courtesy of Wolverine

Wolverine Blvd Cap-Toe Boot


5. Dr Martens 1460 Panel Leather Lace Up Boots


Of course, when you’re discussing men’s casual boots, you’re going to add Dr. Martens in the mix.  We’ve mentioned in other articles how their combat boots are very comfortable and have a timeless appeal. 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 of course the book comes with a Goodyear welt.

dr-martens-1460-panel-leather-lace-up-boots Courtesy of Dr Martens

Dr Martens 1460 Panel Leather Lace Up Boots


6. Kenneth Cole The Life-Lite Hiker Sneaker


The very word “casual” denotes a relaxed attitude; and these sneaky hiker sneakers are totally kickback cas. 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.

Kenneth-Cole-The-Life-Lite-Hiker-Sneaker Courtesy of Kenneth Cole

Kenneth Cole The Life-Lite Hiker Sneaker


7. 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, 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.

UGG-Neumel-Chukka-Boot Courtesy of Nordstrom

UGG Neumel Chukka Boot 


8. 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° storm welt waterproof that is sealed against rain, snow, mud, and muck. The outer is crafted from waterproofed Horween leather that is soft to the touch.

Allen-Edmonds-Freeport-Weatherproof-Lug-Boot Courtesy of Allen Edmonds

Allen Edmonds Freeport Weatherproof Boot

$311.50 $445.00 30% OFF

9. 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.

Timberland-Port-Union-Waterproof-Boot Courtesy of Nordstrom

Timberland Port Union Waterproof Boot


10. 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 hit the streets in the 40s. While they’re 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. They have a Goodyear welt and can be re-soled.

Dr Martens Vegan 101 black Felix ankle boot Courtesy of Dr. Martens

Dr. Martens Vegan 101 Felix Ankle Boots


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