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 2021.
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
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.
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.
You can never go wrong with clean white sneakers and Artisan Lab has just the pair. The brand's '70s-inspired high-top trainers are hand-stitched in Italy and boast a slim profile, fuss-free design and super soft yet durable Italian calfskin construction with Margom soles for durability.
Uniform Standard is renowned for its elegantly understated designs, and its Series 4 model is no different. Crafted from a combination of premium Italian suede and recycled materials, including recycled rubber and recycled cellulose, these minimalist high-tops are equal parts stylish and sustainable. Plus, a padded topline collar ensures ultimate support and comfort.
These Italian-made high-tops from Hardgraft draw inspiration from classic baseball styles, but offer a luxurious artisanal touch, with handcrafted crepe soles, velvety Italian suede uppers and a soft supported insole with a 1cm heel. Flexible and oh-so-comfy, they're the perfect everyday shoes.
These velvety suede sneakers from German leather goods label Dalgado are meticulously handmade in Portugal from only the finest materials, including biobased suede for the upper, full-grain calf leather for the lining and Italian Margom rubber for the outsoles. The sleek silhouette will pair perfectly with just about anything – from your casual weekend uniform of jeans and a tee to sharp tailoring.
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's Chuck 70 High Top is an updated take on the iconic 1970s design, featuring an added cushy insole for arch support and stability and wing tongue stitching on 12oz canvas for durability. Classic and oh-so-cool: you can never put a foot wrong in Chucks.
Dutch label RoyalRepubliQ's Court High-Top is a vintage-inspired design with clean lines and considered construction, making it a year-round go-to, whether you're relaxing on the weekend or commuting to the office. A memory foam insole with calf lining offers extra comfort for all-day wear.
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.
Discover our pick of the best minimalist sneakers for men.
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