Retro Sneakers that Will Never Go Out of Style

Nostalgia may be harmful. Looking back at the good ol’ days can distract you from what’s now and next, and that’s usually a bad thing. Retro trainers are not a good idea when it’s about fashion.

Many of the best sneakers are older than you. The classic silhouettes that often originate in sports and find their way into casual clothing have remained unchanged for decades. Some of the ones on this list are even older than 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 join the fun? Before you buy the latest Supreme collaboration or take out a second loan, you should check out some of the best retro shoes you can still purchase today. All of these styles have their own unique history and have basically paved the road for other sneaker designs. They are the classics, the trainer world’s equivalent to Shakespeare and Marlowe – the originators and still the best.

Canvas Sports Shoe

The shoe is made to be worn for sports. 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. Chuck Taylor wore Converse hi-tops in his first college basketball match in 1919. In 1922, he was hired as a Converse sales representative and travelled all over the United States to sell the canvas shoes which still bear his signature.

The early Chucks were made with standard shoe leather outsoles, and midsoles weren’t yet available. 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.

Tennis Shoe Minimalist

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. Stan Smith? No Common Projects. There are versions of this shoe from most brands, and even other racquetsports have produced retro trainers (the Converse Jack Purcell stands out).

Pharrell West and Kanye west, both of whom have worn this style in the past, are also big names from the sports world, including Andy Murray.

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.

New Balance M320, the world’s number one running shoe. Runner’s World In 1976, you’ll know) or designs by Adidas Diadora Puma which keep the vintage appeal but without the decades-old scent.

The Football Casual Trainer

The football casual, which is part of the larger boom in sportswear in recent years has become a popular reference point for designers as well as streetwear children. Bucket hats have returned. Stone Island, Sergio Tacchini and bucket hats are back. The terrace trainer is back.

Adidas has a trio of stars, the Hamburg Samba, and Gazelle, that are the league leaders in this style. All sleek but bold nonetheless, they were practically standard issue on the British football stands in the ’80s and ’90s. You can look out for T-shaped toe panel and extra points if you have traditional suede uppers with gum soles.

Reebok Classic: Beyond the three stripes is your 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. You can wear them with a pair of slim jeans, a shirt, and optionally a pint diluted lager.

Skate Shoe

Vans shoes were used for work wear before you tried your first kickflip wearing a pair of beaten up Vans while Sum 41 played on your old phone speaker. Vans was founded in Anaheim in California. Twelve people purchased Vans #4 Deck Shoes, now known as Authentic, on the day of their opening in 1966.

Vans’ reputation began to explode. 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. Converse One Star and Nike‘s Blazer, which both offer a similar silhouette and styling.

Basketball Hi-Top

The best basketball shoes, according to some hypebeasts aren’t meant to be worn on the court, or even off. They should be framed and hung with pride like your school portrait is in your grandmother’s house. Adidas and Reebok both have some iconic 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 first pair was created in 1984, for Michael Jordan. Since then, there have been hundreds. 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. There are many variations.

Streetwear and hip-hop looks work best when you combine chunky basketball shapes with off-court silhouettes. Denims, joggers and statement jackets are all great options. Simple t-shirts, simple denims, and joggers will let your shoes do the talking.