The 2025 Way to Wear Sneakers This Winter

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Outfit inspiration inside.

It’s official: Sneakers aren’t taking a break this winter. While boots usually dominate cold-weather wardrobes, this season’s most stylish dressers are rewriting the rules with fresh, sneaker-forward outfits that feel effortless yet intentional. Think classic kicks paired with statement outerwear, roomy trousers, and textural layers—it’s comfort dressing but elevated. The key isn’t just the shoes themselves but what’s worn with them. Every outfit we’ve saved lately has one thing in common: an oversize element that makes the whole look feel current.

From slouchy bombers to structured maxi coats, the proportions this winter are big—literally. The oversize layer gives sneakers that fashion-girl balance of relaxed and refined, transforming what could be a casual outfit into something street style worthy. Pair clean white sneakers with an exaggerated trench and puddle pants, and suddenly you’ve hit the sweet spot between minimalist and cool. It’s proof that volume can look chic, not sloppy, when done with purpose.

Even traditionally “polished” pieces are getting the oversize treatment this year. Tailored blazers come boxier, knits are intentionally roomy, and even denim is cut with generous ease. The sneakers keep everything grounded—quite literally—making the oversize proportions feel wearable instead of intimidating. The contrast between streamlined shoes and a voluminous silhouette is what makes these outfits stand out in a sea of predictable winter looks.

So if you’re refreshing your wardrobe for the final stretch of 2025, take this as your cue to lean into scale. Swap your slim jeans for wide-leg versions, trade cropped jackets for sweeping coats, and let your sneakers be the understated anchor that ties it all together. The end result is effortlessly modern and quietly cool—the exact kind of look that earns double-taps and repeat wears.

See the coolest ways to wear your sneakers this winter below and shop our favorite styles along the way.