Modernized Athleisure

Sneakers will forever be an essential when it comes to sporty-chic athleisure. (But we’d be lying if we said it was the only choice, thanks to Uggs.) “There are so many options for loungewear and matching sets—you can go preppy, colorful, or classic off-duty, all of which beg for a chunky tech dad sneaker,” says Anthopologie head of styling Kyla Flax. “I love this look for traveling too—just throw a blazer or long wool coat over the sweats to feel polished.”

Boho Chic

If you’re a millennial, the idea of wearing a loose, oversized shirt might feel far out of your comfort zone—but it fits right into the effortless, bohemian style that’s taken over as of late. New York City-based stylist Audree Kate López says to give it a whirl: “I like styling an elevated item, such as a midi or maxi skirt, with an oversized, unexpected top like a graphic tee, shacket, sweater, or blazer, then grounding the outfit with a sneaker,” she reveals. “It’s not all fancy, and not too casual: It’s a nice in-between where you feel put-together, effortless, and cool.”

Not Your Dad’s White Socks

Tall white socks have been the norm with gym sneakers for the past few years. Now, we’re also seeing calf socks alongside more everyday sneaker silhouettes. The combo feels unserious and mildly nostalgic, pulling at our Y2K-loving hearts.

As for what to pair your sneakers and tall socks with, the options are endless. Nevertheless, Flax loves the idea of a dress: “One of the easiest ways to tackle transitional dressing is by pairing a versatile dress with sneakers,” she confirms. “From a romantic slip dress with suede Puma Speedcats to something more everyday, like a flowy shirtdress with a colorful Gola, it’s an easy way to feel practical with a cool girl edge.”

Classic Combo

What’s more classic than a pair of sneakers? Combining your kicks with denim and a plain white tee. “You can’t go wrong with sneakers and denim,” Flax says. “Opt for straight leg jeans in a vintage wash, layered with a cardigan or bomber jacket and paired with colorful, retro slim sneakers. It’s timeless yet still feels fresh.”

Playful ’90s Favorites

In recent seasons, fashion has been a bit of a scrapbook of relics from the ‘90s and early ‘00s. Think: Baggy boyfriend jeans, low-rise silhouettes, statement shoulder pads (bonus points if you opt for a trending hue like chartreuse), and pops of silver—you know the drill. Something we love about all of these things? They pair unexpectedly well with sneakers. 

Serious Fashion Business

Once upon a time, suits were reserved for business meetings and formal gatherings, two places where sneakers haven’t historically been welcome. But today, these staples are an ideal pairing—just ask López. “Suiting has come back in a less serious way the past few years, and I love styling oversized suiting with sneakers,” she tells us. “Maybe you have a matching suit, or you’re dressing up an outfit with a blazer. The juxtaposition of a sneaker is cool, relatable, and gives that ’90s corporate commuting aesthetic.”

Flax agrees: “I love grounding a tailored look with sneakers—think wide-leg trousers, a crisp button-down, and a cropped trench (which will be huge this fall),” she says. “Finish this look off with a ’90s throwback style like Asics, Reebok, or New Balance.”

Pattern Play

Try styling sneakers with coordinating prints to make them stand at the forefront, as opposed to an afterthought. Classic Adidas kicks pop against a striped skirt and statement tee, especially if you opt for organza laces to add a touch of sweetness.

Effortless It-Girl

Slip dresses aren’t the only silhouettes suitable for pairing with sneakers: López likes the looks of maxi skirts and dresses of pretty much all cuts. “For fall, I love focusing on intentional layers, especially during the early moments when it can be chilly in the morning and a warm summer day by the afternoon,” she says. “Pairing a midi or maxi dress with sneakers grounds the look. You can add light layers like a jacket, cardigan, or blazer on top, or layer a lightweight turtleneck, button-down, or long-sleeve underneath.”

Modern Diana Uniform

You know the beloved Princess Diana baggy sweatshirt and bike shorts combo we all return to each spring and fall? To elevate this go-to, consider trading your sweatshirt for some cozy knitwear and your spandex shorts for something a smidge more tailored. “I’ll throw on an oversized sweater with longer Bermuda shorts, then finish the look with ballet-inspired sneakers,” Flax says. “It keeps things playful and casual while still feeling seasonal.” Another option? Micro-tailored shorts, like the fun chartreuse ones above.

Day-to-Night Drama

Remember: Sneakers go with anything—including silk jackets and chiffon gowns. It’s all about rocking your look with confidence. “I love that we are getting more experimental with mixing and matching items that don’t seem to go together—like sequins and athleisure—and the perfect way to dip a toe into this is practicing the wrong shoe theory,” López says. “Grounding your fancy look with the balance of a sneaker can transition a fancier or night-out item into daytime.”

Some of her favorite unexpected high-low sneaker pairings? A polo and sequin skirt; a structured jacket, scarf, and mini skirt; and a feather-trim skirt or metallic gown. “It’s fun, unexpected, and a million times more comfortable than pairing these outfits with heels,” she adds.

Street Style Icon

Last but not least, we have athleisure’s slightly dressier sister: the daytime mini (skirt or dress, that is). “During fall, I love bringing the notorious night-out item to daytime with sneakers and a casual top, such as a crewneck grey sweater, a blazer, or a leather jacket,” López shares. One look at the sneakers, body con mini, and varsity jacket above, and we see exactly why it’s a winning combo for transitional seasons.