We Review 9 Stylish Men’s Winter Boots For 2020

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Setting my sights on style, I spent time researching the best men’s winter boots that weren’t tossing style for full functionality.

While I do need boots that will keep my feet warm when I’m out enjoying winter activities, there are times when a stylish pair of boots are more important than whether my toes stay toasty.

Since I’m just the guy to give you stylish mofo’s advice, I wanted to list my top choices for boots you’d be proud to wear picking your girl up on an important date, or for a night out with the guys.

Here are what I consider to be the best and most stylish men’s winter boots for the upcoming year of 2020.

Happyshop Genuine Leather Martin Boots


With choices like wine red, black, and army green, you could buy a few pairs for different events if you wanted. I liked these boots because they’re a bit different from the regular style of boots.

I definitely don’t want to follow the pack when it comes to my footwear. These boots have a woven style that I was really drawn toward. They’re made of genuine leather with wool on the inside as well as a comfort insole.

Ariat Men’s Easy Street Lifestyle Boot


Whether you choose aged bronze or graphite as your color, these leather boots are a beautiful addition to your closet. They’re imported leather with a duratread sole.

They provide ankle support with the high shaft of 8 inches, while the heel is 1.5 inches. The foot is full grain leather with brushed detail on the toe.

The upper part of the boots are suede, which is a beautiful interplay on the top of the boot with the leather.

Columbia Men’s Whitefield Omni-Tech


While the previous pair of boots was pure style, this pair is part style and part functional. There’s 200 gram of insulation in this boot with the suede upper.

There’s an Omni-Tech waterproof membrane to keep your feet dry. They’re lightweight with cushioning for extended walking, while also having great ankle support.

Imagine you’re taking a city walking tour in the late fall. These are the perfect boots.

Caterpillar Colorado Walala


This nubuck men’s boot is made of canvas throughout , from the microfiber sock liner to the upper part of the boot.

The sock liner provides cushioning and comfort while the outsole is made of durable rubber for walking through snow and across ice.

There’s no way you’ll slip with these stylish boots on your feet.

Feature Pick

Happyshop(Tm Men’s Genuine Leather Fashion Round Toe Pull On Short Boots Warm Martin Shoes (Eur 38, Brown)

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Men’s Caterpillar Colorado Slouch Walala Boots

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Serene Men’s Casual Leather Lace Up Soft Breathable Fashion Oxfords (8D(M)Us, Coffee)

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Overland Sheepskin Co Men’s Dolny Wool-Lined Leather Boots

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Serene Mens Stylish Suede


These boots come in a variety of colors from coffee brown, to blue, to black, or red brown.

Personally, I like the coffee pair. While they look like leather, they’re made of synthetic materials, which means they’re more durable.

The sole is rubber, and has wide lugs to ensure they’ll grip and provide great traction.

They’re lace up with a side zipper to keep them tight and secure around the ankle.

Men’s Overland Dolny


These boots are made of cowhide leather that has been oiled to look vintage. There’s a leather overlay and a contrast top stitch for a great design on the boots.

The heel strap and rounded toe complete the look of this stylish boot.

The interior has natural wool that will ensure that your feet are warm throughout the cold winter months. The sole will keep you from skidding on slick surfaces.

YFFaye Men’s Christams Martin

YFFaye Men's Christams New Winter Fashion Martin High-cut Lace-up Boots

The Martin high cut boots are available in dark blue or coffee, with a top layer of leather.

There’s a rubber sole that provides slip resistance for walking on ice or snow. The lining keeps the feet warm as well as comfortable. 

Men’s Ankle Buckle Boots


While these look like supple leather, they’re made from synthetics. The lugs are made of rubber to provide a sure-footed walking surface.

The lace up boots have stylish buckles on the backs that give these a different look than traditional winter boots. You won’t be afraid to wear these in the fanciest of restaurants with your date.

They come in a chocolate brown or black, with brown soles for contrast.

Serene Men’s Leather Buckle Boots


These leather boots are made with attention to detail. The welt stitches and contrasting materials keep these from being a plain brown or black pair of boots.

They have a buckle in the back that will cinch the boot tight for winter wear. They’re not exclusively for winter, though. They can be worn anytime you want to look your best.

The lace up boots have a rubber sole that will keep your feet from slipping across many surfaces. You can walk across the damp ground and head indoors without worrying about slipping on either surface.

Many of these boots are suitable for cold weather conditions, though, they shouldn’t be subjected to large snowbanks in the dead of winter.