8 Men’s Winter Boots You’ll Wear All Season
Don't forget about your feet
best winter boots for guys

By Gabi Meyers | Last Updated: Nov 22 2019

I’ve seen it too many times in the winter: guys’ otherwise great surrendering to ugly-but-warm footwear that’s utilitarian at best. 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, boots can also be plenty fashionable. 

With it snowing in some places since October this year, you may already be in a scramble to find new cold weather footwear. So we’ve rounded up the best warm, insulating boots that are also handsome enough to enhance your outfit. Don’t believe me? Read on.

Check out these eight men’s winter boots you’ll wear all season long:

1. Ugg, $190

ugg harkley weatherproof boot

SG Says: Starting this list out strong! And reminding you NOT to sleep on every girl in college’s favorite winter boot brand, Ugg. These boots look good enough to wear all day, while the waterproof finish with sealed seams helps you stay dry and warm this winter.

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

2. Sorel, $89-243


SG Says: Obviously we had to include this iconic winterwear brand in the mix, but wanted to break out from the Sorel Caribous you see everywhere these days.

The flexible canvas upper on this pair changes the style game, while remaining as insulating as the cold weather brand you’ve come to know and love.

3. Red Wing, $290

red wing winter boot

SG Says: When shopping for investment pieces, look for minimalism and quality. These Red Wing boots offer both, and in ten years will only look better than the day you bought them.

4. L.L. Bean, $150


SG Says: How beautiful are these L.L.Bean 10″ Bean Boots? If you want winter footwear that will last you forever and is somehow even more heritage-y than the 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.

Pro Tip: The 6-inch version, while stylish, can and will get your ankles wet, so we recommend the 10-inchers to be safe (and decidedly more British). Which, b-t-dubs were $220 last year and this winter are selling for only $150 a pop. What a steal!

5. Danner, $317-336


SG Says: I don’t know about you, but I first discovered these beautiful boots on the cover of Cheryl Strayed’s breakout memoir Wild (maybe you saw Reese Witherspoon in the film adaptation?).

A vision of beauty in the eyes of any seasoned hiker, these bad boys are the footwear of stylish survivalists. If you’re going to camp on a mountain and fight a bear, or just make your way 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. Quoddy, $350

quoddy sperry boots

SG Says: Like the Bean Boots, these babies hail from Maine, so you know your toes are covered for winter weather…literally.

7. Lacrosse Ice King, $180


SG Says: Hmmm… looks familiar. They’re not Bean Boots, and they’re not Sorels… they’re familiar… yet… so… different.

Born in La Crosse, Wisconsin (hi!) in 1897, this boot brand has been outfitting farmers, hunters, and construction workers for over a century. And they’re the second cheapest pair of boots on this list, so hi! twice.

8. Pajar Gearson waterproof boot, $175

best men's winter boots

SG Says: If you like your winter boots to look and feel a bit more like a sneaker, this pair from Pajar 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.


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!


Finding the perfect winter boots for you

If you’re ready to upgrade your winter footwear but dread the thought of shopping for new shoes…consider shopping with Team SGHonk honk, it’s the best!

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