High-top sneakers: how to wear them

High-top sneakers have been around for a century, first on basketball courts and later on skateboards, stages and city pavements. They keep returning to fashion because they solve a simple problem: they make a casual outfit look deliberate. Below we look at where the modern high-top came from, how to wear one today without looking like you are off to the gym, and what to check before buying.

A short history of the high-top

The canvas high-top began life as a sports shoe, designed to support the ankle during quick changes of direction. Over the decades it moved from the court to music scenes, from punk to hip-hop, and from there into everyday wardrobes. Leather versions brought a cleaner, more grown-up look, while suede and printed canvas made them a fashion object in their own right.

The hidden-wedge moment

In the early 2010s, high-tops took an unexpected turn. The French designer Isabel Marant popularised a sneaker with a wedge heel concealed inside the shoe, so that from the outside it looked like a sporty high-top while adding several centimetres of height. Her suede styles with Velcro straps and contrast panels became one of the most talked-about shoes of the period and were widely imitated on the high street, in every colour and print imaginable: leopard, metallic, neon and florals.

The appeal was easy to understand. A hidden wedge gave the leg-lengthening effect of a heel with the relaxed attitude and comfort of a trainer. The trend has since calmed down, but it left a lasting idea: sneakers can be a styling choice, not only a practical one. If you still own a pair, our outfit idea with floral high-top wedges shows how to wear them now.

How to wear high-tops today

With skinny or slim jeans

This is the easiest pairing. A narrow leg tucks neatly into the shoe or sits just above it, so the whole silhouette stays streamlined. Roll the hem once if the jeans bunch at the ankle.

With straight or wide jeans

A straight leg should fall over the top of the shoe or be cropped just above it. Avoid hems that stop halfway down the collar of the sneaker, which cut the leg awkwardly. With wide jeans, a chunkier high-top balances the volume better than a slim canvas style.

With dresses and skirts

High-tops add a welcome casual edge to a feminine dress. Midi and knee-length dresses work particularly well: the gap of bare leg (or tights) between hem and shoe keeps the look light. A simple black dress, a denim shirt and sneakers is a combination we return to often, as in our guide to the denim shirt worn five ways.

With cropped trousers

Cropped tailored trousers and a clean leather high-top create a smart-casual look that works for many offices. Keep the trousers slim and let a little ankle or sock show.

With socks

Socks can be part of the outfit. A plain white or grey sock just peeking above the collar looks fresh; a ribbed sock in a contrast colour adds a playful note. Avoid socks that slouch halfway down and wrinkle around the shoe.

Choosing a pair

A few more points to check in the shop:

• Fit at the ankle. The collar should hug without rubbing the ankle bone. Walk around and flex your foot.
• Sole thickness. A thin vulcanised sole is light and classic; a thicker cupsole gives more cushioning for long days on foot.
• Colour. White, black and navy go with almost everything. A colour or print is more fun but works best when the rest of the outfit is quiet.
• Fastening. Laces offer the most adjustable fit; zips or straps make them quicker to put on.

Caring for high-tops

• Brush off dirt after each wear, before it settles in.
• Spray leather and suede with a protective product before the first outing, testing it on a hidden area first.
• Clean canvas by hand with mild soap and a soft brush rather than putting it through the washing machine, which can weaken glue.
• Stuff with paper to keep the shape and absorb moisture after a wet day, and let them dry away from radiators.
• Wash or replace laces now and then; fresh laces make old shoes look new.

For white pairs, which need a little more attention, see our guide to white sneakers care and styling.

The bottom line

High-tops are versatile because they sit between sport and style. Keep proportions in mind (narrow leg tucked, wide leg over or cropped), let them contrast with something more polished, and look after them so they stay crisp. That is all it takes to make a pair earn its place in your wardrobe for years.

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