Skip to main content

6 Ways To Style High-Top Sneakers

With these tricks, you can get away with wearing them every day of the week.

High-top sneakers first burst onto the scene in 1917, when Converse released the now-iconic All Star, a shoe that quickly became a favorite among basketball players and other sports enthusiasts. The original idea was that the extra material extending past the top of the foot would provide extra ankle support that could reduce risk of sports-related injuries. Shortly thereafter, basketball star Chuck Taylor suggested some design changes, which the company accepted, and Taylor officially endorsed the shoe that would come to bear his name.

Since then, every brand under the sun has created its own iteration of the shoe, from dirt-cheap Canal Street knockoffs to this $132,000 pair from luxury shoemaker Buscemi. High tops have become a mainstay for sneaker heads and fashion lovers the world over, even if they can't name a single team that plays in the NBA. Still, it can be difficult to know what to wear them with.

Got a pair or two of high tops in your own closet? Here, we rounded up some of our favorite ways to style the classic silhouette with a modern twist.

With cropped pants

One of the easiest ways to rock your high tops is by pairing them with the cropped jeans you already love wearing every day. Whether the bottom of the pants are rolled up, cut off or just hemmed a little shorter, the ideal length of pant will hit about two to three inches above the top of the shoe when you're standing up. This works well for anything from your classic skinny to a more relaxed boyfriend fit, but looks especially of-the-moment with straight- or wide-leg pants.

With a girlie skirt

It feels a little outdated to call sneakers "boyish" in light of the increasing gender fluidity of the world we live in, but suffice it to say that they add a nice sense of balance to the frillier confections in your closet. Throw on your high tops with a floral, pleated, lacy or pink skirt to infuse even the princessiest look with a dose of downtown cool. Add a varsity jacket for even more striking contrast.

Scroll to Continue

Recommended Articles

With an oversize hoodie

There is possibly nothing more comfortable than wearing an oversize shirt, hoodie or sports jersey as a dress and foregoing pants — why else would it be so many people's sleepwear of choice? Luckily, it's also very on-trend at the moment as an acceptable wear-outside-the-house look, so there's no better time to embrace your inner comfort-lover. Pair your most hype hoodie or jersey with a classic pair of high tops, throw on a baseball cap and you're good to go.

With workout gear

When you're headed to the gym, comfort and function should be your first wardrobe priorities. Thankfully, elevating your look to the next level doesn't have to mean compromising. Pairing your high tops with even the simplest pair of leggings and an athletic top can come across as an intentionally minimalist statement, and can easily transition to whatever errand is next on your agenda when you throw a leather jacket over the top of it all post-workout.

With funky socks

Even the simplest high tops tend to make a statement, so take advantage of the extra attention on your feet. Up the ante by adding a pair of bold socks that peak out over the top of your sneaks. Fishnets, patterns and quirky trim are all worth trying, and don't be scared to mix things up — try rocking an unexpected combination, like delicate lace with your most street-savvy urban kicks. 

With your comfiest dress

On days when you want to cheat the look-professional versus feel-great dilemma, slip your high tops on with a cozy knit sweater or T-shirt dress. You can add polish to the look by pairing it with fancy accessories or a designer bag, but won't have to deal with any of the uncomfortable pinching or pulling of your more structured outfits. Just keep your sneakers clean and mark-free if you plan to debut this outfit in an office setting.

Never miss the latest fashion industry news. Sign up for the Fashionista daily newsletter.