High-top sneakers have been a staple in casual-cool fashion for decades. These sneakers may have started as athletic shoes, but they quickly moved into the fashion world as the ultimate statement shoe. From Chuck Taylors to Air Jordans, high-tops say that you’re an approachable person who still has an impeccable sense of style.

Anyone can stick on a pair of high-tops, but wearing high-top sneakers like a gentleman is an art. Read on to learn how to style your high-tops so you can keep your look fresh no matter the occasion.

With Jeans

High-tops with jeans is a classic look that never goes out of style. It’s a casual, laid-back look that still keeps you looking sharp and shows the people around you that you know how to dress well. But if you want to make this look work for you, you need to make sure you’re wearing the right type of jeans. 

The platinum rule of styling high-tops like a gentleman keeps your ankles visible; this is not the place for loose, baggy jeans. Opt for a skinny jean or at least a slim fit with a close-cut ankle in a classic wash. Keep the rest of the outfit simple with black or white high-tops and a solid-color crew neck t-shirt, preferably white.

With Chinos

If you want something a little more dressed-up than jeans but not as formal as a suit, it’s hard to go wrong with chinos. These casual khakis walk the line between classy and casual, giving you a little more flair than a pair of jeans. And with high-tops, they strike the perfect balance of put-together and approachable.

When putting together this look, stick to tan or navy chinos in a slim fit that’s a little more relaxed than skinny jeans. Cuff the chinos to show off your shoes and top the look off with a plain or striped polo or Oxford shirt. Keep the shirt untucked, or go for the always-popular French tuck look.

With Shorts

You might want to keep things on the more casual side or to beat the heat on a summer day. Wearing shorts with high-tops can be tricky to pull off, but with the right styling, you can make it work for you. The key is to keep the rest of your outfit looking high-quality and neutral.

Shorts break the usual high-top styling rules since these shoes look best with shorts that fit looser. You also want to go with a looser shirt since the visual focus at your ankle will be so tight. Stick to black and whites for your shirt, and keep shorts above the knee and in denim or neutral tones.

With a Suit

A suit and high-tops are the chocolate-covered pretzels of the fashion world. These two opposites pair beautifully and balance each other out well, contrasting the laid-back confidence of the shoes with the elegance of the suit. But you have to pick the right combination for this outfit, or you’ll wind up looking less suave and more sloppy.

Make sure your suit is well-tailored and fits close at the ankle; sagging pants will not work here. Pick solid-color high-tops, preferably in neutral tones like black and white. Pair patterned or brightly colored high-tops with a white t-shirt, tailored slacks, and a matching blazer for something a touch more casual.

With Active Wear

As much as high-tops have become a fashion statement, they got their start as basketball shoes. You can keep that origin story going when you pair your high-top sneakers with activewear. This will be a very casual look, although it will give you a more intentional and contemporary look than normal sneakers.

For a more trim look, pair high-tops with a pair of slim leg track pants and a black t-shirt. If you have a chunkier high-top shoe, go for basketball shorts and a stylish jacket over the top of a loose t-shirt. Try to keep these clothes high-quality to avoid looking like you just walked off the court.

Keep It Clean

The key to wearing high-tops like a gentleman is to keep the rest of your outfit clean. High-tops are already something of a statement piece, and you want to give them the room they need to speak. Don’t go for brightly colored or patterned shirts, and keep your lines simple and tailored.

It’s also a good idea to wear reasonably high-quality clothes when you’re putting together an outfit with high-tops. Sneakers are a casual shoe, and you need to offset that by showing people you can appreciate the finer things in life, too. Good-quality clothes can help to elevate your high-tops and keep you in that balance between casual confidence and effortless elegance.

Wear Your High-Top Sneakers Like a Gentleman

High-top sneakers can be an amazing fashion accessory, but you have to style them right if you want to pull off that look. Keep your outfit clean, focused on neutral tones, and fitted pieces. Make sure your ankles always show, and opt for higher-quality clothes when you can.

If you’d like to discover more tips for wearing high-top sneakers like a gentleman, check out the rest of our site at Kickscrew. We have every shoe you could dream of, from Nike and Adidas to Yeezys and Converse. Shop our Converse shoes today and step up your fashion game the Kickscrew way.

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