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Find the right men’s slip-on winter boots for every occasion

These men's winter boots are easy for slipping on and off

Man on steps in boots
Jacob Townsend / Unsplash

Winter is nearly upon us, and that means we are frantically getting in the last few rays of sunshine. As we spend as much time as possible outside soaking up the final rays of fall, we can’t forget to transition our wardrobes from autumn to winter, warm to cold, and light to heavy. While some of us still have a little bit of time before we see the snow and ice, the rains and falling leaves mean it is time to break out some of our favorite winter boots. That also means we have to prepare ourselves to work a little harder when it is time to put on our shoes.

While summer and fall are the time for slip-on shoes like sandals, loafers, and drivers, the winter doesn’t lend itself to that very often. That is; unless you get creative and start looking for the best slip-on men’s winter boots. Of course, as usual, there are tons of options for slip-on boots (many of them are classified as Chelsea boots), but we always have you covered, so our list of favorites is to follow. But first, we need to help you figure out how to prepare those boots for the winter.

Chelsea boot in the woods
Hamza Bounaim / Unsplash

Protecting your winter boots from … winter

Before picking out your favorite boots to get ready for the winter, you should know how to take care of them. Some boots are going to be more rubber than leather or come pre-treated, and you may not need to worry about this particular step. But just in case, here are the three things you should do to take care of your winter boots.

  • Clean your boots – Whether this is the first time you are wearing them or you’re breaking them out after a long off-season in storage, your boots need a good cleaning. Most of the time, you just need to brush dirt or grime off the exterior. If you do need to remove stains, you can use an even mixture of water and vinegar or baking soda to remove them.
  • Condition your leather – Once you have removed all the dirt and grime, you need to make sure your leather looks moisturized and healthy. Many of the places you are buying your leather boots from will offer a specific leather conditioner meant for their products. If you are spending the money on boots, don’t skimp on the conditioner.
  • Waterproof your boots – One of the worst parts of winter weather is the feeling of wet socks. You also never want to look down and see your boots ruined by getting wet. The solution is to ensure they are waterproofed and will keep you warm and dry. Similarly to the above, there will be options on most boot sites for a wax or a seal that is best for the boots you choose.

Now that that is out of the way, let’s get to the heart of the matter. Here are the best of the best slip-on winter boots for your closet.

Nicks Boots Heritage Chelsea
Nicks Boots

Nicks Boots Heritage Chelseas

If you read our article on Nicks Boots and its collaboration with Buck Knives, you probably already know we love us some Nicks Boots. They are some of the toughest boots on the market, chosen by many of the Pacific Northwest’s bravest firefighters. You may not need them to fight fires, but these slip-ons will bridge the gap between comfort, ease, and protection.

Duluth Trading LaCrosse Aero Insulator
Duluth Trading Company

Duluth Trading Company LaCrosse Aero Insulators

Helping people do is what Duluth is about, and getting you psyched to do everything that you need to do and everything you know someone else won’t do for you is why you elect its products. Work doesn’t stop because the snow hits the ground, so you need boots that are tough enough and secure enough to keep you on the road or in the field long enough to get it done. That’s why they offer LaCrosse’s Aero Insulators. Wherever you find yourself in the snow, these boots can handle it, as they are rated for temperatures as low as -60 degrees Fahrenheit. And it isn’t just for your feet and ankles, as the fleece-lined shaft reaches all the way up your calf to keep you as warm as possible.

Huckberry XTRATUF Deck Boots
Huckberry

Huckberry XTRATUF Deck Boots

Ever watched Dealiest Catch? If you have, then you know how tough of a life Alaskan fishermen lead. They need something they can rely on when the worst that Mother Nature can muster is thrown at them. Their choice is deck boots. Ready for rain, snow, mud, and yes, ocean swells, these deck boots from Huckberry are exactly as the name implies, extra tough. If they are good enough to be the choice of one of the toughest vocations the world as ever seen, then they’re good enough for your deck as well.

Kodiak McKinney Chelseas
Kodiak Boots

Kodiak McKinney Chelseas

You know who knows about snow? Canadians. And Kodiak has taken its Canadian roots and created one of the better boot companies in the world. Since 1910, Kodiak has kept those brave enough to leave the comfort of the cabin to venture into the blizzards safe and warm. The McKinney is one of its most popular boot models, and this Chelsea version doesn’t skimp on the structure and protective aspects (like the signature Double Gore or abrasion-resistant lining) in search of comfort.

Ariat Groundbreaker Work Boots
Ariat

Ariat Groundbreaker Work Boots

There are some people who just understand what hard-working men need when they are keeping the world moving forward. Farmers and ranchers fall into that category, and they have trusted Ariat for the last 30 years. We don’t give the Western boots enough credit as go-to work boots. This particular model is designed to handle construction, factory, warehouse, or farm and ranch work. Fun fact, Ariat got its name and inspiration from the one and only 1973 Triple Crown winner Secretariat.

Timberland Redwood Falls Chelseas
Timberland

Timberland Redwood Falls Chelseas

From the moment Timberland made its first yellow boots, it became one of the most classic and sought-after boots on the market. All year round, people in the Northeast would flock to get themselves the iconic look. Now it has created new winter boots that take the style of the classic yellow boots with the comfort and ease of slippers. The Redwood Falls model works like work boots with the style of Chelseas, making them perfect for your everyday boots.

Carbon2Cobalt Range Boots
Carbon2Cobalt

Carbon2Cobalt Range Boots

Carbon2Cobalt is one of the first brands you should look to if you are an Adventurer-style archetype. It is rugged, functional, and effortlessly cool. The company’s mission is to be classy, stylish, and comfortable. These range boots are the perfect representation of what they are. Combining Western and motorcycle stylings, these boots are going to change the way you see winter. You never know, you may even start looking forward to it.

L.L. Bean Duck Boot Chelseas
L.L. Bean

L.L. Bean Duck Boot Chelseas

L.L. Bean has been making functional outdoor and hunting boots since before World War I. And one of its best is these duck boots. While it has evolved over time to include many versions, this Chelsea adaptation is still hand sewn in Maine with all the rest. One at a time. The existence of these boots proves one thing: They do still make things like they used to.

Now that you have picked the winter boots that are going to make your life warmer, dryer, and more stylish, all you need to do is put the snow tires on your car. We can’t help you there.

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Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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