8 Men's Winter Boots You'll Wear All Season

Don't forget about your feet

By Gabi Meyers | Last Updated: Feb 20 2019

When it comes to men’s winter boots, “stylish” isn’t necessarily top of mind when shopping. Each day from December through….say March?!, millions of guys’ outfits across the globe surrender in the face of ugly-but-warm footwear that’s utilitarian at best.

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. 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. Sorel, $140


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.

2. Red Wing, $290

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.

3. Timberland, $395

SG Says: Oh snap, you thought we were going to post those yellow Timbs that literally everyone has been wearing for, like, ever. Think again, because these Earthkeepers are way more dapper, and BONUS: you’re way less likely to run into a footwear twinning situation while stomping around the snow in them.

4. L.L. Bean, $220

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).

5. Quoddy, $450

SG Says: These leather beauties are the most luxe on this list, and probably the choice boot for any #teamSG sneakerheads reading. Why? Because every inch of this boot is customizable, meaning every pair is rare. Like the Bean Boots, these babies hail from Maine, so you know your toes are covered..literally.

6. Lacrosse Ice King, $170

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.

7. Chippewa, $290

SG Says: Hold up, do we have another Wisconsin-based boot on this list? You bet your ass we do. Historically, Chippewas are designed for the local logging community back in Chippewa Falls, WI, yet have gained a following among the hypebeasts of the world. Thankfully, you don’t have to be a waiting-in-line-at-Supreme sneakerhead OR a Midwesterner to wear them (though you might want to grow an affinity for cheese curds and argue for the merits of Miller Lite over Bud Light just to truly complete the ensemble).

8. Danner, $360

SG Says: Last, but certainly not least, I present to you these beautiful Danner boots. I first discovered these 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 survivalists. If you’re going to camp on a mountain and fight a bear, these are without a doubt the boot you want to wear while doing both.


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:

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.

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