Versatile, comfortable and always on trend, high-top trainers are a must-have casual staple in every man's wardrobe. Scroll on for the ultimate guide to ankle-hugging kicks, including how you should be styling them and our pick of the best high-tops for men in 2023.

A brief history of the high-top trainer

The origins of the high top trainer can be traced back to 1917, when the now-ubiquitous Converse Chuck Taylor All Star first made its debut. Initially invented by Marquis Mills Converse, it was redesigned in 1922, when a basketball player by the name of Chuck Taylor approached the company, complaining of sore feet and asking them to create a better shoe with increased support and flexibility. After Converse added Taylor's signature to the ankle patch, the iconic Chuck Taylor All Star was born.


The athletic promise of high-top trainers was quickly established, and other brands began releasing their own sporty takes, from the iconic Nike Blazer, one of Nike's first dedicated basketball trainers; to the Reebok Freestyle, the first athletic shoe designed for women; to the Vans Sk8-Hi, the world’s first high-top skate shoe.

Inevitably, as sportswear became integrated into mainstream style, high-tops were adopted off the court, serving a purpose well beyond function and entering the realm of fashion. Today, most sneaker brands offer performance-based basketball trainers as well as lifestyle lines that pay a nod to the sport but are more appropriate for the street. Limited-edition colourways, retro rereleases, and revamped silhouettes leave contemporary sneakerheads drooling

How to wear high-top trainers

All too often, high-top trainers are written off as difficult to pull off or simply "not for me", but we're here to reassure you that anyone can – nay, should – wear them, it's just a matter of knowing how best to style them. It depends on whether you're wearing a chunky silhouette or something more refined, but generally, it's best to opt for a slightly cropped trouser style, with the cuff sitting on the top of the sneaker to showcase it.

Play with proportions and try wearing a pair of high-tops with shorts, socks that come just above the sneaker and whatever you desire on top – a workwear-inspired overshirt will lend your outfit a touch of utilitarian style.

Despite their athletic roots, the relaxing of dress codes makes high-top trainers ideal for smart-casual occasions, or even a business-casual setting. Team a pair of sleek leather high-top trainers with an Oxford shirt and tailored trousers for an effortless professional look, or wear them to a relaxed summer wedding with a softly tailored suit.

Best men's high-top trainers to buy in 2023

Velasca Ghisa Sneakers

Made in the Italian shoemaking district of Montegranaro, these high-top trainers from Velasca epitomise the Milan-based brand's commitment to craftsmanship. Crafted from super smooth calfskin leather with a box bottom rubber sole, they're casual yet elegant, easily dressed up or down.

CLAE Walrus Brown Leather Gibson Sneakers

These high-top sneakers from LA-based footwear label CLAE are almost boot-like, thanks to their sturdy leather construction. The rich brown colour makes them the perfect shoes for autumn and winter: team them with a chunky knit, woollen socks and your go-to denim jeans for a cosy and stylish solution to cold weather dressing.

Converse Vintage Canvas Chuck 70 High Top

Converse's Chuck 70 High Top is an updated take on the iconic 1970s canvas sneaker design, featuring an added cushy insole for arch support and stability and wing tongue stitching on 12oz cotton for durability. A classic sneaker that remains oh-so-cool: you can never put a foot wrong in Chucks. Plus they are extremely democratic and affordable for most budgets.

JAK Atlas Sneakers

Portuguese brand JAK specialises in super sleek sneakers that occupy the space between smart and casual. Case in point: These Atlas sneakers, which are minimally designed but offer maximum comfort, thanks to a cemented and stitched sole and removable shock-proof innersoles. The elegant leather upper will help you look the part at all times. Team them with selvedge denim jeans and a worker jacket for an updated take on workwear style.

LØCI Ten Sneakers

While more mid-top than high-top, LØCI's Ten sneakers definitely deserve a mention here, for their planet-friendly construction and easy-to-wear streetwear inspired style. Crafted from vegan materials and 100% recycled plastics, they offer an effortless way to tread lighter. Team them with baggy jeans and a slouchy hoodie for instant skate park-approved style.

Cariuma Canvas OCA High Sneakers

Renowned Brazilian footwear label Cariuma has taken its iconic OCA style and given it a contemporary update, with the addition of lightweight cushion technology, a flexible yet durable rubber sole and cool cap-toe design. The all-black colourway is clean and simple, lending these sneakers ultimate versatility for just about any occasion.

Crown Northampton Abington Hi Toe Cap

Drawing inspiration from classic basketball footwear silhouettes, Crown Northampton presents the Abington Hi Toe Cap. This minimalist high-top trainer style is expertly hand crafted in England from full grain calf leather with a durable sidewall stitched sole unit, so you can expect them to endure for many years.

Axel Arigato Dice Hi Sneaker

These chunky men's high-top trainers from contemporary Swedish brand Axel Arigato are inspired by vintage styles, with a decidedly modern twist. Team them with ribbed socks, drawstring shorts and a classic heavyweight tee for a fail-safe casual summer look.

Discover our pick of the best minimalist sneakers for men.