6 Retro Sneakers That Will Always Be Cool

Nostalgia can be a terrible thing. Looking back at the good ol’ days can distract you from what’s now and next, and that’s usually a bad thing. Not when it comes to fashion, though, and definitely not when it comes to retro trainers.

The best sneakers are often ancient, older than your dad. Classic silhouettes, often originating in sport and finding their way into casual dress, have remained relatively unchanged for decades (there are some on this list close to seeing out a century). Whether you’re trying to look throwback or not, these designs have stood the test of time – and they’re not going anywhere soon.

Over the past five years we’ve seen the trainer industry explode. The UK footwear market alone is predicted to grow to around £9.5 billion by 2022.

Want to get in on the action? Well before you jump on the next Supreme collaboration and take out a second mortgage, check out the best retro sneakers you can still buy today. These styles all boast their own distinct history, and have essentially paved the way for all other sneaker designs today. They are the classics, the trainer world’s equivalent to Shakespeare and Marlowe – the originators and still the best.

The Canvas Sports Shoe

A sports shoe made to play actual sports in. Who would’ve thought it? Yes, before limited drops of overpriced sneakers designed by high fashion’s hype names, people wore sneakers to exercise in. In 1919, Chuck Taylor played his first college basketball game in a pair of Converse hi-tops, and in 1922, was hired by the company as a sales representative, travelling all over the States selling the now-iconic canvas shoes that still bear his name.

This was before midsoles had been introduced and those early Chucks had outsoles made of standard shoe leather. Practically everything else has stayed virtually unchanged in the decades since: the soft, unstructured upper, white rubber toecap, distinctive round branding – a genuine design icon that has rolled with every sneaker trend in the decades since, all the way up to 2018’s clear Off-White Virgil Abloh Chuck Taylor.

But Converse isn’t the only brand that produced an all-star canvas shoe in the first half of the 20th century. Italian footwear brand Superga introduced its 2750 model in 1925, Slovakian brand Novesta has been in the game since the ’30s and Pro-Keds produced its first basketball shoe in 1949.

None of them could be called performance trainers in today’s world of energy-return soles and flyknit uppers, but they’ll always look good. They can be punk or preppy, hip-hop or rock n roll and they’re one of the few things in your wardrobe that tend to look better with age.

The Minimalist Tennis Shoe

Adidas’s all-time best-selling shoe took its bow on the tennis court. In 1965, what we now know as the Stan Smith was named after another player, Frenchman Robert Haillet (it was changed after Haillet’s retirement). But many of the design hallmarks – the perforated three-stripe logo, achilles cushioning and contrast green on the heel – were there from the start.

Tennis has been a rich source of sneakerhead lust because the sport’s traditional all-white dress code spawned something most men now have somewhere in the foot locker: the minimalist white sneaker. No Stan Smith, no Common Projects. Most brands have a version of it and even other racquet sports have contributed some retro trainers that have stood the test of time (the Converse Jack Purcell being the standout).

Still worn by big sports names like Andy Murray, this style has also branched out into the world of hip hop through the likes of Pharrell Williams and Kanye West, who have both served them up in the past.

The Retro Runner

With tracksuits and other throwback sportswear very much in fashion, it’s no surprise that the best running shoes from decades past are also jogging to the top of wish lists.

You can’t talk about running shoes and not mention the Nike Cortez. Hailed as the first modern running shoe thanks to its revolutionary design by Olympic track coach Bill Bowerman, it includes a raised foam heel to safeguard runners’ Achilles tendons during long distances, as well as a thicker than normal rubber sole for resilience.

What were once considered performance shoes are now impractical heavyweights, but they look great with cuffed jeans or chinos, even if you’re unlikely to break your half-marathon PB in them. For styling, think suede and leather patchwork uppers and muted colours that contrast sharply with the bright tones worn by today’s athletes.

Check out the classic M320 from New Balance (named as the number one running trainer by Runner’s World in 1976, you know) or designs from Adidas, Diadora and Puma, which all keep the vintage appeal without the decades-old smell.

The Football Casual Trainer

As part of the wider boom in sportswear, the football casual has been a reference point for designers and streetwear kids in recent years. Bucket hats are back. Stone Island and Sergio Tacchini are back. And so too are terrace trainers.

Adidas is the comfortable league winner in this style with its trio of superstars, the Hamburg, Samba and Gazelle models. All sleek but bold nonetheless, they were practically standard issue on the British football stands in the ’80s and ’90s. Look out for the T-shaped toe panels and score extra points for traditional suede uppers and gum soles.

Beyond the three stripes, the Reebok Classic is your obvious super-sub. Another champion of the ’90s it has been adopted by the streetwear scene in recent years. Or for something different, try a training shoe that made it as a spectator shoe like Puma’s Astro Cup. Whichever side you support, style them with slim jeans, a polo shirt and, optionally, a pint of watered-down lager.

The Skate Shoe

Before you were attempting your first kickflip in a beaten pair of Vans whilst Sum 41 blared from your archaic phone speaker, they were actually used as a workwear shoe. The original Vans shop was based in Anaheim, California, where on the first morning of its opening in 1966, 12 people purchased Vans #44 Deck Shoes (now known as the Authentic), which were manufactured that day and made available for pick-up in the afternoon.

From there, Vans reputation exploded. Disneyland, not so far from the original store, supplied Vans footwear to the park’s workforce, starting off with all-black pairs made for employees on the monorail. Then they gained a reputation within South Cali’s skating community, mainly for their rugged design and grippy sole, which were ideal for sticking to the decks of their boards.

Fast forward to today and Vans is still the world’s best loved skate shoe brand, and away from the decks, the brand’s styles have become a modern, casual replacement for smarter footwear to pair with tailoring. If Vans are too ubiquitous for you, try Converse One Star or Nike‘s Blazer, which both offer a similar silhouette and styling.

The Basketball Hi-Top

For some hypebeasts, the best basketball shoes are not to worn, on court or off. They should be framed and hung with pride like your school portrait is in your grandmother’s house. Adidas and Reebok have some cult shoes but Nike‘s really the MVP here – and few retro sneakers of any kind have the kind of cult-like appeal of its Air Jordans.

The range stretches back to 1984 when they were first made for Michael Jordan. There have been hundreds of iterations since. It’s a classic silhouette and just enough of a blank canvas for continuous updates and collabs – utter catnip for collectors.

But Jordans weren’t the first iconic basketball sneaker. Pre-dating MJ’s many releases was Nike’s Air Force 1s which came in the early ‘80s, and were the first pair of basketball shoes to have a pocket of air inside the soles. Again, the variations are countless.

Off-court, chunky basketball silhouettes work best with hip-hop and streetwear looks. Think relaxed denim, joggers, statement jackets and simple tees that let your footwear do the talking.