6 Cute Outfits with Sneakers to Wear This Winter

Cropped feet view of model wearing a women's Alex Sneaker in Drizzle Grey shown.

There's a lot to love about sneakers, from the comfortable feel, effortless aesthetic, and endless versatility. But one thing that really stands out about this footwear category is that with endless options of sneakers for women, it's suitable for year-round wear. 

We appreciate that seasonless sneakers transcend from warm-weather women's shoes to a laidback ladies' footwear option during the chillier months. There are endless styling possibilities in the winter, but if you're stuck on ideas, we're here to assist.

Keep reading for a roundup of cute outfits with sneakers, along with styling tips and helpful insight into the various types of tennis shoes.

How to Style Cute Outfits with Sneakers in Chilly Weather

Whether you're in the market for new trainers or have a favorite pair sitting in your closet waiting to be worn, you've come to the right place. Flattering everyone with an effortlessly cool vibe, these footwear staples will likely always have a place in fashion.

Tennis shoes go with virtually limitless ensembles. Still, it's not always easy to curate different looks, especially when cold weather hits.

Wondering how to style cute outfits with sneakers during the chilliest time of year? It's safe to say the footwear fanatics at TOMS know a thing or two about sporty shoes and streetwear, and we're here to guide the way.

Our best-loved looks include jeans, dresses, leggings, jumpsuits, athleisure, and even business casual wear. Ahead, six cute winter outfit ideas to rock with sneakers.

1. Express Yourself in Dressed-Down Denim

Want outfit inspiration for how to wear sneakers with jeans? Like tennis shoes, jeans go with almost anything and look good on pretty much everyone. Not only that, but both can be worn 12 months of the year. Needless to say, sneakers and denim are a stellar combo, and there are many routes you can take with this look.

Start with your favorite, most flattering pair of jeans—whether they're black, white, skinny, high-waisted, wide-leg, bootcut, or ripped—and curate your ensemble from there.

If you're wearing skinny jeans or an otherwise fitted cut, you can choose between a loose-fitting top or a tighter shirt. On the other hand, slouchier pants look great when balanced out by tighter tops.

Most outerwear styles go with jeans too. Consider a wool peacoat, leather jacket, cropped puffer, bomber, or tailored blazer. Then throw on a beanie or scarf to finish the look.

What Sneakers Go with Denim?

Sneaker booties are always a solid choice when wearing jeans in the winter. If you're going for a chic look or are wearing pants with a wider ankle, your best bet is leather or suede slip-ons, which are a cross between flats and sneakers.

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2. Combine Sporty and Flirty in a Dress

Can you wear sneakers with dresses? Yep! Even in the winter? You bet! While it's true that tennis shoes are an inherently sporty footwear category, they've evolved into more of an everyday style.

To successfully style sneakers with a frock during the chilly season, start by choosing a winter-friendly dress. Maxi or midi cuts in heavier fabrics will offer the most warmth. Shorter dresses can work, too, though you might want to wear tights or nylons.

When heading out the door, throw on a wool overcoat, trench, or a knee-length raincoat if precipitation is on the forecast. If you need an extra layer of warmth, put on a slouchy sweater, a long cardigan, or a button-down underneath.

Opt for a maxi or midi dress in colder weather and a sundress in the summer to style with sneakers for a blend of flirty and sporty. 

What Sneakers Go with Dresses?

The best tennis shoes to wear with dresses in the winter are trainer-boot hybrids. We recommend platform sneaker booties. To keep your toes cozy and make a cold-weather fashion statement, you can rock a pair of tall knit socks with or without tights.

3. Live Leisurely in Leggings

Leggings have become a ladies' wardrobe staple, especially during the fall and winter. They're flattering on all body types, exceedingly comfy, and endlessly versatile—what's not to love?

Since leggings are form-fitting and pocketless, it's generally best to wear them with a somewhat long, loose-fitting top. Our favorite options include slouchy cable-knit sweaters, thigh-length cardigans, drapey blouses, flannel-button downs, and oversized crewneck sweatshirts for a sportier look.

Cropped feet view of model wearing Lug Platform Sneaker shown.

What Sneakers Go with Leggings?

A better question would be, What sneakers don't go with leggings?—which is to say, you've got tons of choices. Flat-soled sneaker boots offer a laid-back appeal, while low-top lace-ups are an excellent everyday choice. For a bit more height, go with sneakerized platform shoes.

4. Dress to Impress in a Jumpsuit

Like dresses, jumpsuits are not only fashionable but also convenient. As a one-piece ensemble, all you need when wearing a jumpsuit in the winter is a warm coat and a cute pair of kicks.

For professional or semi-formal settings, slip into a peacoat, trench coat, blazer, or a dressy rain jacket. If you're aiming for a casual look, go with a denim jacket, leather coat, or a traditional rain slicker.

What Sneakers Go with Jumpsuits?

We adore platform sneaker boots with jumpsuits, as they offer warmth and height while keeping the bottoms of the pants dry. Prefer a flat sole? You can't go wrong with classic slip-ons.

5. Go Ultra-Comfy in Athleisure

Love leggings? Take your comfort a step further with head-to-toe athleisure. Everyday sporty apparel has officially been accepted as street clothes, and we're here for it.

Whether you're partial to yoga pants, running tights, joggers, performance shirts, mesh tops, track jackets, half-zip fleece coats, coordinated sweatsuits, or all of the above, it's easy to throw together athleisure outfits.

You can also pair regular pieces with athleisure wear. Think button-downs, basic cotton tees, knit sweaters, crop tops, denim jackets, puffers, leather coats, trenches, and rain jackets.

What Sneakers Go with Athleisure?

One of the best things about athleisure wear is that it goes with active trainers and fashion sneakers alike. With casual wintertime outfits, reach for a pair of low-top canvas or leather tennis shoes. On-trend platform lace-ups will elevate your ensemble while adhering to a sporty vibe.

6. Look Polished in Business Casual

While it varies among employers, tennis shoes have become an acceptable business-casual footwear option in many offices. For the rest of your ensemble, go with pressed slacks, high-waisted trousers, khakis, or potentially dark-wash jeans if they're allowed.

On top, throw on a pressed button-up blouse, a flowy shirt, a fitted sweater, or a mock-neck shirt. Generally speaking, tailored shirts will make you look more polished and put-together by balancing the informality of your shoes.

In the winter, you can wear a wool overcoat, peacoat, blazer, sports jacket, or a trench to complete your nine-to-five look. Expecting rain? Reach for a sleek navy blue or camel rain jacket.

What Sneakers Are Business Casual?

If you've yet to wear tennies to the office, we suggest fashion sneakers over performance styles to avoid looking overly laid-back. Consider a sneaker-flat hybrid like canvas alpargatas or leather slip-ons. Additionally, always make sure your shoes are clean and scuff-free.

Comfy, Stylish Sneakers from TOMS

As you can see, there are many types of sneakers for women and tons of ways to style sneakers throughout the winter. They go with everything from jeans, jumpsuits, and pants to summer dresses, leggings, and athleisure. A cute outfit inspiration can be a simple tee, your favorite pair of pants, and sneakers, or switch it up for a sundress and sneakers. 

If you're looking for the perfect pair to wear with any of these outfits, you should definitely browse the selection of sneakers for women from TOMS. We also carry boots, wedges, platforms, and everything in between and many of our styles are also treated for water resistance to keep your feet dry in wet weather.

Visit us at TOMS for more inspiration from how to style a sundress with sneakers to how to wear wedge sneakers and Shop our collection today!

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Reviewed By Dan Caves

Dan Caves is the Senior Manager of Digital Marketing at TOMS and has been operating in the digital space for 6 years, writing about the latest trends or styles and helping brands make bold statements with innovative tactics and creative concepts. He's determined to go all the places, see all the things, and pet all the dogs.