When it comes to winter footwear, the average weather-appropriate stepper doesn’t exactly score high on the sartorial charts. Uncomfortable, clunky shoes and boots (not to be confused with chunky-heeled — these are straight up style gold) might protect your feet from the elements, but they can also put a frumpy twist on even the most fabulous of getups — a major bummer. Because your style sensibilities shouldn’t have to go into hibernation during the colder months, we’ve put together 10 pant + shoe pairings that can stand up to a little less-than-ideal weather without cramping your style.
1. & Other Stories Ankle Strap Boots ($245) + Zara Cropped Trousers ($70): Snow boots might not be necessary, but keeping those feet covered up once the temps take a plunge is a must. And ankle boots will do you right every time. Slipping on a pair of low-cut wool socks will help help bridge the gap between cozy and chic. For bottoms, think cropped to show off your topnotch steppers, but stick with pairs that fall closer to the ankle than the knee, to minimize exposure.
2. Dolce Vita Gael Wedge Ankle Boot ($130) + Madewell Flea Market Flares ($135): When you want to go a little more casual, a suede wedge bootie is where it’s at. A pair of corduroy flares will fall perfectly over the shoe’s elevated silhouette, while adding the subtlest hint of throwback flair to your look.
3. Zara Platform Bluchers ($50) + M.i.h Jeans Linda Trouser ($435): Rugged sole bluchers give you the grip you need to handle slippery sidewalks. Cropped trousers will put the ultra polished pair front row and center, though wide leg bottoms can totally hold it down here too.
4. F-Troupe Lace Up Boot ($255) + H&M Imitation Suede Pants ($60): Burgundy lace-up booties with a hot-right-now-meets-Victorian-era appeal will keep the cold weather at bay all season long with their tough treads. Pair them up with slim trousers in a soft (faux) suede fabric for a dressed-up edge.
5. & Other Stories Chunky Platform Leather Shoes ($195) + Mango Button Flared Trousers ($90): Platform loafers serve up a double whammy of style and utility this season. Thanks to the elevated base, toes are out of the way of slush, sleet and snow — plus you get a bit of a boost without having to don a pair of steep stilettos. Toss ’em on with wide leg bottoms for a modern take on a mid-century ensemble.
6. Aldo Rodway Sneaker ($100) + BDG Corduroy Slim-Fit Pant ($59): A little bit sneaker and a little bit boot, these warm winter kicks will keep feet cozy and comfortable no matter what your commute throws their way. Style them with slim-cut corduroys — cuffs ever-so-slightly rolled up — for an effortless look that’ll do you right in and out of the office.
7. Eeight Emily Blue Furry Shoes ($120) + Wilfred Jallade Pant ($145): Your go-to black booties have a track record of keeping your winter look on lock, but this season go the extra style mile with unexpected accents like bright blue faux shearling. Pair them with high-waisted slacks in a warm flannel fabric — they fall just above the ankle to make sure everyone gets a peek of those standout steppers. Add on an oversized knit and you’ve got one killer 9-to-5 look.
8. Aquatalia by Marvin K. Odina Weatherproof Boot ($495) + J.Crew Skinny Stretch Cargo Pants in Aubergine ($98): When the layers and heavy coats come out, make sure you have a pair of knee-high boots on hand. The tall style instantly imparts a layer of cold weather cool to any outfit. Opt for weatherproof options when you can or invest in some heavy duty protectant to keep them looking fly. Stick with skinny jeans or trousers with these ones to create a sleek, streamlined silhouette (it’ll be easier than cramming those BF jeans inside too).
9. Sperry for J.Crew Shearwater Buckle Boots ($180) + Chimala Chino Single-Pleated Trousers ($265): When the need for snow boots becomes inevitable, make sure you’re whipping out a pair that your inner fashionista would be proud of — like this color blocked shearling-accented set. Skinny trousers and jeans are an obvious pairing, but for a look that packs a little more edge, opt for relaxed fit chinos. Roll ’em up like you would your fave pair of boyfriend jeans and pair with an oversized button down, statement baubles and a long menswear-inspired coat.
10. Charles & Keith Duo-Textured Booties ($73) + Mango Zip Trousers ($80): Channeling those cool, tough-girl vibes is incredibly effortless come winter with leather-look pants and #girlboss approved two-tone booties. Perfect for the office or off-duty, pair up the look with a flowy top or chunky knit to create unexpected contrast.
What are your go-to winter shoes when you’re not rockin’ standard snow stompers? Tell us in the comments!
