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.”
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.
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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.
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.”
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
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.
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.
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.
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.
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
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.