(Style)

9 High-Top Sneaker Outfits For Crisp Fall Weather

Keep those ankles covered.

by Laura Lajiness Kaupke
Jeremy Moeller/Getty Images Entertainment/Getty Images
A high-top sneaker outfit with a blazer, crop top, and trousers.

Whether you’re a longtime sneaker die-hard or fresh to the scene, fall undoubtedly calls for a dip in the high-top sneaker pool. Yes, boots are a signature of the season and one of those closet staples you can’t wait to revisit when cool weather hits, but they’re not always the mood — especially heeled or knee-high versions with a decidedly formal feel. Instead, when an inherently effortless look is the goal, an outfit with high-top sneakers is a stylish default.

Some come sporty, from color-block Nike’s to three-stripe Adidas, to the iconic Converse All-Stars. But high-tops can also read polished — sleek leather silhouettes are key in this case. Namely, ultra-minimal designs in black and white. Nostalgic silhouettes á la the ’80s and ’90s are another route to achieving flawless high-top sneaker style in the fall, like a reissued design for the 2020s or an inspired-by take with a modern, techy approach. When taking this high-top look for a spin, it’s particularly on-point with leisurewear for a Princess Diana fashion moment.

What’s more, high-top sneakers just so happen to be one of fall’s biggest sneaker trends, and according to Megan Stephens, Anthropologie’s senior footwear buyer, they’re timeless, too. “High-tops are a classic must-have staple for your season-less wardrobe,” Stephens says. “They’re the perfect transition piece for your wide-leg pants into fall, and they extend the life of your summer mini dresses with a cropped cardigan and ruffle socks. From classic and clean to sporty, the expansive range is what’s fun about high-tops now.”

(+)
Edward Berthelot/Getty Images Entertainment/Getty Images
(+)
Christian Vierig/Getty Images Entertainment/Getty Images
(+)
Edward Berthelot/Getty Images Entertainment/Getty Images
1/3

So, whether you’re looking for new ways to wear your favorite childhood styles or finally adopting the above-ankle silhouette into your wardrobe, keep scrolling for nine stylish high-top sneaker outfits suited to fall’s crisp weather. Plus, insight from Stephens and an edit to shop — each one is perfect for keeping those ankles covered in the chilly season.

We only include products that have been independently selected by TZR’s editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.

Casual Dress

Jeremy Moeller/Getty Images Entertainment/Getty Images

At the top of the season, Stephens suggests pairing high-top sneakers with “summer minidresses, a cropped cardigan, and ruffle socks.” Or, try a seasonally fit sweater dress on days when you’re not in the mood to layer.

Denim Days

Edward Berthelot/Getty Images Entertainment/Getty Images

For many, the perfect high-top and denim look involves a pair of cropped wide-leg or kick-flare jeans — the ensemble is effortless with a white t-shirt and trench when there’s a mild chill. For more of a textured look, Stephens says, “cozy high-tops are the perfect complement to your straight leg denim and a chunky sweater.”

Leather Weather

Christian Vierig/Getty Images Entertainment/Getty Images

Fall is officially leather weather, and what better way to lean in than with a slouchy pair of trousers, slick high-tops, and a uniquely cropped sweater?

Do The Diana

Christian Vierig/Getty Images Entertainment/Getty Images

For a vintage-inspired athleisure vibe, Stephens says, “Go full Princess Diana and rock biker shorts with a slouchy sweatshirt and the APL Defenders.” Once it’s too chilly for shorts, swap for a stylish pair of sweats and top the look off with an oversized blazer.

Cozy, Elevated

David Dee Delgado/Getty Images Entertainment/Getty Images

The sweater dress is unquestionably one of fall’s easiest pieces. Make yours more dimensional by layering leggings underneath with high-tops and a tailored coat to finish.

Menswear Inspired

Jeremy Moeller/Getty Images Entertainment/Getty Images

When embracing menswear styling for fall, you can’t fail with a boxy blazer, ankle-skimming trousers, and high-top sneakers for a low-key tailored vibe. Or, work more texture into the equation — Stephens suggests cropped wide-leg corduroy pants and a roomy button-down.

Matchy-Matchy

Claudio Lavenia/Getty Images Entertainment/Getty Images

No high-top sneaker look is more visually impactful than one styled around matchy-matchy separates. Go full-on with a coordinating top, skirt, and coat, or simply start a matching sweater set.

Easy Tailoring

Melodie Jeng/Getty Images Entertainment/Getty Images

Tailoring doesn’t always mean stiff. Try teaming wide-leg or flared trousers with an elegant hip-length coat and leather high-tops for a slick but oh-so-hip finish — the result amounts to a comfortable work-to-wherever outfit.

White Jeans For The Win

Claudio Lavenia/Getty Images Entertainment/Getty Images

White jeans instantly refresh any denim fatigue you may be feeling throughout the season. Keep them fall-appropriate by pairing yours with tonal high-tops, a button-down shirt, and a dark coat for some contrast.