How To Wear High-Top Sneakers Without Looking Like A Kid

A woman in a black shirt and pants, blue crop jackets, and white high-top sneakers

In 1917 Converse introduced its All Star basketball shoe, the world’s first high-top sneaker. Fast forward more than 100 years and this now-iconic footwear silhouette remains as relevant as ever. Sure, the athletic focus of these ankle-hugging sneakers has dissipated for the large part, but brands across the spectrum (contemporary, designer, high street) offer stylish, street-appropriate riffs on the high-top sneaker that keep our imaginations inspired and wardrobes stocked.

With the rise of athleisure in recent years past you’ve likely got a stash of sneakers in your closet that you probably style with separates like floral dresses, blue jeans, and just about everything else. Still, we’ll be the first to say that wearing high-top sneakers can oft prove to require a bit more mental effort than its no-frills, low-top cousin. Perhaps it’s because we want to avoid cutting ourselves off at the ankle or because they add so much heft to any outfit — whatever the case, we’re here for a fashion challenge and we know it can be done.

To help, we took to Instagram to hunt down some of our favorite women in the industry showcasing just how effortless it can be to wear high-top sneakers. Scroll down to load up on outfit ideas and shop a few of our high-top picks of the moment to get started.


Keep to a light, neutral palette with a sand-colored tee tucked into white jeans. Accessorize with a statement bag and, of course, your high tops.

Snag these collaboration sneakers before they sell out.


Give a flirty top a boyish twist with the addition of cropped blue jeans and white Chucks.

Where it all began.


For your next party, consider wearing high-top sneakers with a long-sleeve maxi dress in a eye-catching color, like periwinkle.

The perfect mix of feminine and masculine, if you ask us.


Traveling on foot in a new city? Pair your high-tops with ankle-length pants and a fanny pack for the ultimate no-fuss outfit.

These sleek Superga high-tops go with everything. Trust.


Don't be afraid to lean (very far) into athleisure territory. A fitted tank and a pair of windbreaker bottoms in fall's must-have color keep the look updated.

Get 'em before they sell out. Because they will.


Need a low key look for date night? Style a slinky slip dress with a casual straw bag and off-white Converses.

For the fashion adventurist.


Team an evening dress with French-inspired bedhead and high-top canvas sneakers.

These luxury sneakers can dress up a casual look while simultaneously being able to dress down a formal getup.


Add some color to a floral-print dress and white jean jacket with a pair of tomato-red sneakers.

Enjoy an updated take on the iconic brand's legacy colorway.