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The 10 Best Men’s Slip On Winter Boots for 2022

The world is your oyster when it comes to tracking down all sorts of the best winter boots, including finding an easy-on, easy-off pair of men’s winter slip-on boots. Why this style for the season? Well, frigid weather naturally calls for you to bundle up in a big way, from a base layer to a flannel shirt and a parka. Sometimes, the last thing you want to do is fumble around with lace-up boots, which is where men’s winter slip-on boots can come in very handy.

There are options available at plenty of price points, be it more budget-minded or more luxurious, each designed to hold its own against winter weather while looking surprisingly stylish and even rugged for when the occasion calls for it. Some of these pairs of the best slip-on winter boots for men are geared for going off-trail or taking on work in the yard or the garage, and some of our favorites are a bit more dressy and city-minded. Whatever the case might be, your new favorite pair of winter slip-on boots is out there, of that we’re positive. Outfit yourself accordingly with utility and style in mind this season.

leg of a man wearing a huckberry all weather shoe.

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Best Overall Men’s Winter Slip-On Boots: Huckberry All-Weather Chore Boots

image of Huckberry All-Weather Chore Boot.
Huckberry

When the going gets extremely tough, get yourself some hard-wearing slip-on boots for winter from the minds of the good folks at Huckberry. These feature a rubberized leather rand and extreme weather-fighting capabilities. They’re as trusted as it gets for the bone-chilling cold.

Best Go-Anywhere Men’s Winter Slip-On Boots: Blundstone Original 500 Boots

image of Blundstone Original 500 Boot.
Huckberry

Sometimes, the weather calls for winter boots that are slightly more polished and yet rugged all the same. That’s a specialty of Blundstone, and it only makes sense that these classic slip-on boots are still beloved around the world. Wear them with jeans or canvas work pants any time you need extra protection on the footwear front.

Best Men’s Winter Slip-On Boots for the Great Outdoors: XTRATUF Deck Boots

image of XTRATUF Deck Boot.
Huckberry

If you want next-level performance on slippery surfaces and in tough conditions, you might as well step into a pair of boots that are trusted by fishermen on the high seas. These are adept at providing excellent traction, and they’re 100% waterproof.

Best Winter Slip-On Dress Boots: New Republic Maison Leather Jodphur Boots

image of a New Republic Maison Leather Jodphur Boot.
New Republic

Every now and again — especially if you’re heading back to the office or heading to a formal event — you’re going to need to level up your winter footwear game. Enter the elegant, refined, and highly affordable leather jodhpur boots from New Republic. They’re easy to step into, they look sharp with wool trousers or slim blue jeans, and they’re the epitome of refined comfort and elegance at a low price.

Best Heritage Slip-On Winter Boots: Florsheim Foundry Plain Toe Gore Boots

image of a Florsheim Foundry Plain Toe Gore Boot.
Florsheim

There’s a wide variety of ways you can get dressed this winter, but we appreciate both the ease of stepping into winter boots, plus the sleek style you get from the right pair. These are a heritage-quality pair of winter dress boots, made with famed Horween leather from Chicago, so you’ll have them for years to come.

Best Fashion-Forward Winter Men’s Slip-On Bots: Dr. Martens Paint-Splattered Leather Chelsea Boots

image of Dr. Martens Paint-Splattered Leather Chelsea Boot.
MR. PORTER

If you want to amplify your winter wardrobe in a classic yet modern way, these paint-splattered Dr. Martens blend the durability of the iconic brand with an eye-catching look. The Goodyear-welted sole makes them especially tough and durable.

Other Winter Mens Slip On Boots We Love

Allen Edmonds Himalaya Chelsea Boots

image of Allen Edmonds Himalaya Chelsea Boot.
Allen Edmonds

Warmth in terms of your winter footwear is crucial each and every time you step out the door, which is why we love these shearling-lined Chelsea boots from American footwear pioneer Allen Edmonds. They blend the sleek style of a Chelsea boot with the warmth of shearling boots, and they look excellent with your best winter tailored suit.

Danner Arctic 600 Chelsea Boots

image of Danner Arctic 600 Chelsea Boot.
REI

Danner has packed these boots with all the classic heritage and modern functionality you could hope to find, from comfortable technology to 200 grams of insulation and what they call “winter-optimized outsoles.” They should prove unbeatable for all sorts of winter exploration.

Keen Anchorage III Waterproof Boots

image of KEEN Anchorage III Waterproof Boot.
REI

If it’s hard-wearing construction and 100% winter-ready performance you seek, then Keen has you covered with these durable and hard-wearing slip-on men’s winter boots. They’re overbuilt in a great way, and made for winter’s worst weather.

Cat Footwear Pelton Work Boots

picture of CAT Footwear Pelton Work Boot.
CAT Footwear

Sometimes, you’ve got to tackle your to-do list no matter the conditions outside. These slip-on men’s boots for winter are made for just that occasion, with some of the toughest yet most comfortable designs you’ll find on the market.

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