4 Best Ways to Wear High Top Sneakers This Season

A man wearing high top sneakers

A man wearing high top sneakers | Source: iStock

Converse high top canvas sneakers are one of the most basic and versatile shoes you can buy, not to mention a small yet solid investment. They work well with denim, chinos, and shorts and pretty much any color or shade. Converse Chuck Taylor All-Star is where the high top sneaker trend started: Designed with a rubber sole to aid basketball players as early as 1917, the Chuck Taylor has changed little in almost a century. Worn by rock bands, as much as the sportsman and everyday gents, every man should own a pair of Chuck Taylors.

The only true style mishap that a gent can encounter with these classics is when and if they’re worn to a smart casual event or to work when a dress shoe is required. This basic sneaker does not work well for every occasion and should be worn solely for casual situations.

Here are some general style rules to keep in mind when you’re pairing your high tops:

  • Mix your look with relaxed and slim fitting pants to keep your outfit balanced.
  • Keep them for casual and streetwear only.
  • Though dirty/worn high tops can look seriously cool, for the sake of versatility and sartorial savviness, keep them as clean (and well kept) as possible.
  • The key to nailing high top wear correctly is to never wear pants that cover the entirety of the shoe.

Here are 4 of the best ways to wear the perpetually in-style high top sneaker.

1. With jeans

Probably the most obvious and easiest way to wear your casual footwear is with a pair of jeans. High tops are simply another great sneaker option with the added bonus of extra ankle coverage. One of the only ways that high tops and jeans work is with a pair of tailored straight-slim jeans (make sure they’re not too tight) that you can either tuck into the sneaker or tightly roll to reveal the entire sneaker. It’s pretty difficult to make them work any other way. If you choose a baggy pair of jeans, which we strongly advise against, you’re likely to look very unkempt and like you have no idea what you’re doing. Create your perfect high-top sneaker and jean combo by pairing it with a nicely fitted vintage tee, a lighter cardigan, and your pair of slim-fitted jeans for a hip collegiate style look.

2. Tapered sweats


Sneakers | Source: Converse.com

Similarly, any pair of high top sneakers will pair nicely with tapered sweats to exude just the right amount of street style, and they’re ideal for those who have never stepped onto a basketball court. Be sure to get yourself a semi-fitted pair of sweats that taper at the bottom or ones that you can add a roll to. Pair your high tops with grey sweats, a printed tee, and top it off with a camo field jacket for added street appeal.

3. Fitted cargo pants or chinos

There’s something about pairing high top sneakers with a pair of fitted cargos or chinos that screams casual cool. You have several options on how to rock this look, though we definitely recommend you stick with a classic pair of white Chucks. Pair those white Chucks with a pair of black or grey chinos, a plain or printed fitted tee of your choice, and a leather moto jacket. As for your fitted cargos, stick with khaki or olive, and make sure they’re fitted as well, though these look great with a roll on the bottom. Pair them with a plain tee and a casual sports jacket. A chambray or casual oxford shirt will look great with both pant pairings. Feel free to switch out your pants for each unique pairing.

4. Shorts

You have to be mindful of your Converse and shorts pairing because you may end up looking like a punk rock kid who’s trying to get directions to the nearest Warped Tour. Your best pairing option would be a neutral color high top with either a casual chino short or a cotton-blend jersey short that hits just above the knee cap. To keep the look smart, opt for either a casual oxford in a neutral color like blue or white, keeping several buttons at the top open, or a plain tee. Try not to deviate too much from that pairing to make it work in a sophisticated manner.

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