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 2025.
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 2025
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 Bradley Mid
These men's high-top sneakers from LA-based footwear label CLAE are the ultimate all-rounder. Their sleek minimalist silhouette makes them a versatile option for year-round wear, whether with your everyday attire of jeans and a tee or dressed up with a lightweight suit for a summer wedding. Handcrafted from water-repellent leather, they're built to last.
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 Royal Hi Sneakers
Portuguese brand JAK specialises in super sleek sneakers that occupy the space between smart and casual. Case in point: Their Royal Hi 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. Style them with raw denim jeans and a worker jacket for an updated take on workwear 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.
Oliver Cabell Jabbar High
US sneaker label Oliver Cabell fuses traditional craftsmanship with contemporary style in the form of the Jabbar High, a high-top sneaker with a distinctive aesthetic. Hand stitched and lasted in Italy, the style combines buttery Italian calfskin leather with hard-wearing yet lightweight Margom rubber outsoles for ultimate comfort and durability.
Nike Dunk Hi 85
Nike's homage to their original and iconic 85 silhouette offers a stylish throwback. Boasting classic details and retro flair with a padded high-top collar and grippy sole, they'll provide a vintage-inspired finishing touch to your casual ensembles.
Discover our pick of the best minimalist sneakers for men.
