Great Winterized Sneakers Are Your Best Defense Against the Unexpected

Man, the colder months are a real clusterfuck of emotions for me. On the one hand, there’s nothing I like more than spending my mornings piling on layer after layer of literal heat in a sad attempt to hide my lack of personality with increasingly outlandish outfits. On the other, even the slightest amount of wintery precipitation (let alone anything approaching a full-blown snowstorm) is enough to make me pine for summer again like the feckless reprobate I’ll always be. It’s a fine line, really.

I went to school in upstate New York and it was brutally cold a solid three-fourths of the year. Shit suuucked, dude. I can’t even begin to tell you how miserable it is trudging through a few block’s worth of slushy, snow-lined streets on a routine basis. It’s straight demoralizing. Worse yet, it’s absolute hell on your shoes. By the end of senior year, I would’ve rather whipped a Zamboni to class than ruin another pair of precious sneakers. All that’s to say, I’m no novice when it comes to picking out a winter-ready boot alternative, so take it from me: If you can get away with wearing winterized sneakers this season, wear ’em, and wear ’em often.

You can’t live in boots, man. (Don’t get me wrong, you definitely still need a pair.) But if the comfort of your footwear is going to be the deciding factor when it comes to figuring out whether you’ll be leaving the house this winter, a sneaker—or, hell a sneaker-boot hybrid—might be more your speed. So invest in one. Because there’s no worse feeling than cheffing up the perfect fit only to realize you can’t rock the sneakers you had in mind when there’s two and half inches worth of miserable-looking sleet water on the ground.

And hit me up if anyone’s trying to go 50/50 on that Zamboni. I’m still super down.

Advertisement – Continue Reading Below

Sk8-Hi MTE



When Vans began the process of revamping its legendary high top silhouette it set out to make a perfect winterized sneaker—incorporating water-resistant leather uppers, heat retention layers, and a vulcanized lug outsole for added traction—and I’ll be damned if it didn’t come close. 

Shando Sneakers

New Balance


New Balance’s updated take on the classic hiking shoe might not offer the same sort of winter weather detailing as some of its counterparts included here, but the style’s treaded soles and added traction make it ideal if you’re looking for an all-season shoe that can seamlessly transition to tackling the worst of the outdoors on a whim. 

Winter Chuck Taylor All Star



A few years ago, Converse started teaming up with the weather-proofing fabric savants at Gore-Tex to upgrade some of the brand’s most iconic silhouettes, including the Chuck Taylor. Extra water-wicking features—and a pitch-black colorway—render an already durable shoe damn-near indestructible. 

Wool Runner-Up Mizzles



The internet’s favorite sneaker brand is back at it again, tweaking its hero product ever so slightly via a water repellent high top style made out of the company’s now-signature merino wool.  

Converse Edition ‘I Am The Soloist’ Sneakers



This fall, the good people over at Converse went a little collaboration crazy, teaming up with a veritable who’s who of formidable design talent to winterize some of the brand’s best silhouettes. Japanese designer Takahiro Miyashita opted to really go for it, adding just about every detail you’d want in a hulking sneaker style that’s not technically weather-proof but can still handle whatever you throw at it with ease. 

A-COLD-WALL* High-Top Sneakers



Across the pond, team A-Cold-Wall* did up another all-time silhouette in a leather and suede take I’d be loathe to call even remotely winter-ready were it not for the fact that these bad boys look like they’d beat the elements in a one-on-one fight, every damn time. 

Ultra Fastpack III Mid

The North Face


With its exactingly engineered waterproof membrane and Vibram outsole, The North Face’s excellent take on the style offers a seamless marriage of form and function in a silhouette that’ll keep your feet toasty all winter long. And really, if you can’t trust The North Face to make an absolute unit of a sneaker-boot, who can you trust?

Limited Edition XT-6 ADV Sneakers



It shouldn’t come as much of a surprise that your trustiest hiking shoes can play double-duty as a winter-ready footwear option in a pinch. The same features that made the style such a go-to on your socially-distanced walks this summer will serve you well come any inclement weather, and that’s, like, triply true of almost any shoe from Salomon. (Including, say, the brand’s beloved XT-6 sneakers, treaded Contragrip® rubber outsoles and all.) 

500 High Sneakers



No matter how you feel about the man, it’s hard to deny Kanye’s  influence; almost all of the shoes he’s introduced over the years have become iconic in one way or another, reshaping the sneaker market in their after each drop. The brand’s high-top sneaker style has always been a favorite of the man himself, and in a dark grey color way—with key hits of nubuck throughout—it couldn’t look cleaner. 

Terrex Free Hiker



Adidas’ Terrex line makes stylish gear specifically designed to stand up to the worst of the elements, and this hiking boot hybrid—featuring a waterproof Gore-Tex membrane and the brand’s signature Boost technology— is no exception.

Lakke Neal Sneakers



ROA’s Lakke sneakers look like they don’t take shit from anybody, let alone the pesky old elements. Pull-looped and heavily padded, the style comes ready to kick some serious inclement weather ass, Vibram rubber outsole and all. 

Flashtrek Reflective Sneakers



Okay, bear with me here. If you only know Gucci through the Italian label’s wild designer garms, you might be a little skeptical about buying anything else from the brand. You shouldn’t be. Because the label’s unapologetically chunky reflective sneakers (!) come with durable rubber trims and super-thick soles for added traction, making ’em ideal winter-weather candidates if you’ve got the scratch to spare. 

Subscribe to Esquire Magazine

Avidan Grossman is the Style eCommerce Editor at Esquire, covering men’s fashion, shoes, grooming, and accessories.

This content is created and maintained by a third party, and imported onto this page to help users provide their email addresses. You may be able to find more information about this and similar content at

Advertisement – Continue Reading Below

Source : Esquire