The Best Stylish Winter Boots for Men - Style Girlfriend

The Best Stylish Winter Boots for Men

The Best Stylish Winter Boots for Men
Keep your feet looking stylish in the cold

By Gabi Meyers | Last Updated: Aug 12 2022 | 7 min read

I’ve seen it too many times in the cold winter months. A guy surrendering his otherwise stylish wardrobe to ugly-but-warm winter boots.

And I get it! When it comes to men’s winter boots, “stylish” isn’t necessarily topping your list of must have’s when shopping.

But it doesn’t need to be that way.

While cold weather gear is the most functional of all seasonal digs, men’s cold weather boots can also look good! 

Since it’s been snowing in some places since October, you may now be scrambling to find new good winter boots for men.

So we’ve rounded up some of the best winter boots for men. Scroll down to find:

  • The best waterproof boots
  • The best winter boots to wear with jeans
  • The best slip-on winter boots
  • The best winter boots for snow and extreme temps
  • And more!

Here are some of the best quality and most fashionable winter boots for men:

1. Best Waterproof Boots: Sorel, $200

SG Says: Obviously I had to include this iconic winter brand in the mix. But I wanted to share something other than the Sorel Caribous you see everywhere.

That’s not to knock the Caribous, though. They’re great, too. It’s just..if you’re going to buy new boots, why not try a new style?

This pair still boasts the stellar insulation you’re looking for from Sorel. Made from supple waterproof textured leather, these boots have sealed seams, so they’ll keep your feet protected in wet weather.

2. Best investment boots: Nisolo, $260

SG Says: When shopping for investment pieces, look for minimalism and quality. These all-weather Nisolo boots offer both.

And in ten years, they’ll look as good as the day you bought them.

3. Best shearling boots: Ugg, $150

ugg mini classic

SG Says: A gentle reminder NOT to sleep on every girl in college’s favorite winter boot brand.

These classic boots are back, and this time, they’re for everybody.

Truly, this ’90s/2000s footwear fave is totally trendy again. Curious what made them so popular? This is your moment as the style above is now being pushed for both men and women.

And yes, they’re lined inside with the brand’s signature faux-shearling for an oh-so-cozy feel.

4. Most iconic winter boot: L.L. Bean, $199

SG Says: How beautiful are these L.L.Bean fleece-lined Bean Boots?

If you want men’s winter boots that will last you forever and is somehow even more heritage-y than something more pricey like Red Wings, look no further than New England’s favorite winter boot.

Your feet will thank you. Your sons, who are sure to steal them as soon as their feet are big enough (or daughters! Who knows how big their feet will be!) will thank you.

5. Best men’s boot to wear with jeans: Red Wing, $280

Red Wing Shoes  EXCLUSIVE RED WING IRISH SETTER CLASSIC MOC IN RUSSET RED

SG Says: A vision of beauty, these Red Wing heritage boots are pricey, yes, but timeless.

Whether you’re going camping, or just scrambling over a gnarly snowpile on your way to the coffee shop, these are without a doubt the boot you want to wear while doing both.

6. Most punk winter boot: Dr Martin, $160

Dr. Martens 2976 FL

SG Says: These pull-on boots from Dr Marten are lined in faux-fur for a surprisingly luxurious experience for cold toes.

7. Best slip on winter boot: Blundstone, $220

SG Says: Here at SG HQ, we love a Blundstone boot. The #585 style is a classic for cold weather.

8. Best boots for the extreme cold and snow: Sorel, $155

sorel explorer boots

SG Says: If you like your winter boots to look and feel a bit more like a sneaker, this pair from Sorel (yes, another pair) is your poison.

Temperature rated to -22°F/-30°C (!!), these waterproof, seam-sealed boots with a plush faux-fur lining and grippy sole will help you take on winter’s worst.

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So now, you’ve got the boots. What about how to wear ’em?!

How to wear winter boots with jeans

There’s a time and a place for Chelsea boots and chukkas covered, when the weather is sh*t it’s not one of them.

We know what a bummer it is to ruin good shoes, so it’s smart to stick to winter boots when there’s snow, rain, and ice on the ground. That doesn’t mean you can’t still look good, though!

A lace-up winter boot lends itself to a more hearty look, with plaids, flannels, and sweaters topping off your sturdiest jeans.  

Here are a couple outfit ideas for inclement weather:

how to wear winter boots in a stylish way, men's winter boots outfit ideas

SG Says: Don’t think just because you’re wearing boots for bad weather you can’t look good doing it! This chore coat layers nicely under a winter jacket, even over a somewhat bulky flannel shirt.

men's winter boots outfit ideas

SG Says: When the weather calls for a more substantial shoe, keep the rest of your outfit similarly hefty. This is probably common sense and you’re like, Well yeah Gabi, what else am I going to wear, a linen suit?

But you’d be surprised at how often the team sees guys out in the wild wearing rugged af winter boots with a thin sweater or a cotton henley and chinos. Dress for the weather you’ve got, y’all!

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Ready to find your perfect winter wardrobe?

Ready to upgrade your winter style but could use some help? Team SG can help! Schedule a video styling session and receive a customized style plan with a shopping list and outfit direction.

Let us rescue you from shopping fatigue and sartorial apathy. We can promise the kind of personal attention and care that will make you feel like the best version of the awesome guy you already are!

If you’re ready for a daily lewk that’ll change your life, give us a shout.


For more cold weather style, check out SG’s picks for stylish and affordable winter coats