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.
Get the look: Oversize sweater + Jeans + Sneakers
Get the look: Black oversize jacket + Crewneck sweatshirt + Bold pants + Sneakers
Get the look: Baggy trench coat + Layered shirts + Loose trousers + Sneakers
Get the look: Long cardigan + T-shirt + Trousers + Sneakers
Get the look: Baggy pullover + Button-down shirt + Loose white jeans + Sneakers
Get the look: Oversize long coat + Jeans + Sneakers
Get the look: Loose denim jacket + Crewneck sweatshirt + Sporty pants + Sneakers
Get the look: Oversize leather jacket + Sweater + Baggy trousers + Sneakers
Get the look: Chunky winter coat + Loose black pants + Sneakers
Get the look: Oversize sweater + Long pencil skirt + Sneakers
Get the look: Layered oversize T-shirts + Baggy cargo pants + Sneakers
Get the look: Loose button-down shirt + Baggy dark jeans + Leather belt + Sneakers
Get the look: Oversize blazer + White button-down + Loose trousers + Sneakers
Get the look: Baggy tan coat + Sweater + Loose cropped jeans + Sneakers
Get the look: Cropped jacket + Lace top + Baggy trousers + Sneakers
-
I've Given Up Chunky Sneakers, and Only Care About This Trendier Style (and My Favorites are On Sale for Black Friday)Chic. Period.
-
Of All Her Outfits, *This* Hailey Bieber Look Is Stuck in My BrainAnd I will be re-creating it.
-
The Under-$10 Item That Will Dominate All of Winter's Coolest OutfitsAffordable and chic.
-
If You Want Your Sneakers to Look Elevated (Not Basic), Wear Them With These Pants Instead of JeansThis easy swap will work wonders to make your outfits look more sophisticated.
-
The Elevated Pant-and-Top Combo I'm Copying From People in Paris and NYC That's Not a T-Shirt and JeansGuaranteed to make you look trust fund level rich.
-
So *This* Is How We're Wearing Scarves This WinterAnd now you know.
-
Every Chic Woman Is Wearing This "Boring" But Elegant Skirt—Sorry, Minis and MaxisIt's a seasonless staple.
-
15 Cool Denim Outfit Ideas to Get You Through the First Days of WinterCozy ways to style your jeans.
