Retro Sneakers That Will Never Go Out of Style

Flat lay of sport sneakers shoes on the blue and pink background. Fitness background. Healthy lifestyle concept.

Key Points

  • Retro sneakers extend beyond the realm of footwear to become symbols of self-expression.

  • Classic sneakers have a versatility that transcends seasons and style.

  • Retro sneakers provide inspiration for new designs.

The saying "Everything old is new again" is a phrase that makes the most sense when applied to fashion. Every so often, a defunct trend resurfaces years later with new energy. Regardless of how you feel about baggy jeans, belt bags, and wraparound shades, you'll continue to see versions from luxury fashion labels and streetwear brands hit the scene.

This applies to sneaker culture as well. Thanks to brands like New Balance and Asics, dad-adjacent runners have completely taken over fashion week runways, street corners, social feeds, and shop shelves. Who would have thought that '80s-style chunky trainers would be significant enough to build an entire outfit around?

Men's Flair writer Sam Murphy echoes this sentiment: "With their old-school look and feel, [retro sneakers] add a playful edge to any outfit and make a statement without being too loud. And, with so many years of experience behind them, they're also a reliable choice — built to last and supremely comfortable."

Society's love of retro sneakers extends beyond physical attributes. Sure, it's easy to stylize Chuck Taylors with anything you throw at them, be it shorts and a T-shirt, jeans and a hoodie, or trousers and a trench coat, but there's a lot more to it than that. Though you can't measure intangibles like emotions or nostalgia, they're instrumental in how we dress. Retro sneakers bridge the gap between what we currently wear and what we aspire to wear.

You know a sneaker is impactful when remixes come from designers who weren't even around when the shoe was first introduced. Here's a look at some retro sneakers that will never go out of style.

Men's Chuck Taylor All Star

by Converse 

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Converse Chuck Taylor All Star®

It's almost comical to think of a shoe that dates back to 1917 as having the level of influence that this shoe does. Sneakers are a fickle subculture with new models releasing every week, so to have a shoe over 100 years old still be so dominant is quite an accomplishment. It was once an on-court basketball shoe that now stands as a symbol of contemporary style.

A rubber toe cap and vulcanized rubber sole complement the shoe's defining feature: its durable canvas upper. The Chuck Taylor All Star’s tonal base has a simple sophistication that makes it easy to wear with any item but acts as the perfect medium with which to experiment. With its clean, wide-open upper, the Chuck Taylor All Star® has seen creative remixes from everyone, including COMME des GARÇONS and Carhartt WIP to Wacko Maria and Keith Harring.  

White Air Force 1 '07 Sneakers

by Nike

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Nike Air Force 1

Nike's iconic Air Force 1 is a cultural phenomenon that many feel is responsible for pioneering sneakerhead culture. The idea of spending hundreds or, in some instances, thousands of dollars on rare releases got its start with this Nike icon. Part shoe, part fashion statement, and part cultural relic, the Air Force 1 continues to be one of the most sought-after shoes in the market.

The most basic variation of the shoe is a monochromatic white leather upper with a thick midsole and rugged outsole. It has a timeless quality that teams just as easily with track pants and a basketball jersey as it does with chinos and a button-down collar shirt. Its impact stretches beyond shoes and fashion into other creative disciplines, including sports, music, art, and food. Don't just take our word for it. The Air Force 1 has seen reworks by Supreme, Roc-A-Fella Records, Takashi Murakami, and many others.


by Adidas 

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adidas Samba

The adidas Samba is responsible for revolutionizing indoor soccer with a grippy gumsole providing excellent traction on various surfaces. However, its sway as a style accessory outweighs its use as a sports tool. 2023 was a pivotal year for the Samba, especially with the pedestal Wales Bonner put it on for its Spring/Summer 2023 collection. 

One of the common threads uniting all the shoes on this list is versatility. Keep the Samba in the soccer realm and sport it with athletic shorts and a tank top, or put it alongside denim jeans and a leather jacket; the outfit combos are endless. Outside the shoe's multifaceted charm is a stylish sentimentality that resonates with many of today's tastemakers. In 2023 alone, the shoe saw collaborations with Wales Bonner, Sporty & Rich, Palace, and Pharell Williams' Humanrace. 

Suede Classic XXI Sneakers


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Puma Suede

Those around in the '80s know the Puma Suede as a breakdancing shoe. Although the shoe saw time on the basketball courts and soccer fields, some argue that the Suede belongs to urban street communities first and foremost. It has a seasonless appeal creatives in fashion, sports, music, and art gravitate towards.

These shoes sport a sleek silhouette consisting of a plush suede finish with decorative accents hitting the side and heel counter. Puma's famous low-top often gets thrown in the same style category as the adidas Samba, and in that respect, can be worn the same way. Toggle back and forth between sporty ensembles, casual outfits, and smart attire. Those interested in seeing modern takes on the shoe should look to JJJound and Rhuigi Villeseñor. 

Dunk Low By You Custom Women's Shoes

By Nike

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Nike Dunk Low

You know a shoe is popular when memes pop up to stifle its meteoric rise. Regardless of what side of the fence you stand on, the Nike low-cut is arguably the most popular shoe on this list. Your favorite figure, whether musician, athlete, artist, influencer, or Hollywood star, has at one point stepped out wearing them around town.

Initially created as an indoor basketball shoe, the skateboard community took a liking to the Dunk Low's sturdy construction, eventually getting their own variation under the Nike SB umbrella. The shoe even caused a full-on riot in 2005, wreaking Havoc in New York's Lower East Side when sneaker fanatics frantically tried to buy Staple's Nike SB Dunk Low "Pigeon."

Classic Slip-On True White Classics Shoe

by Vans

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Vans Slip-On

No laces, no graphics, no problem. There's something remarkable about minimalist shoes that transcend seasons, styles, and generations. However, when such shoes have the cultural capital that Vans Slip-Ons do, you know you have something special on your hands. Since its introduction in the '70s, the low-top shoe found a home with skate crowds, becoming a fixture on boards throughout the US. The Slip-On's padded collar and vulcanized rubber sole were beneficial in protecting the ankle area while offering extra grip on the board.

Before too long, Vans began treating the upper as a canvas for graphics, opening the floodgates for other artists to do the same. The shoe has been a backdrop for plenty of notable collaborations, including those from mastermind, DIME, Fear of God, Engineered Garments, UNDERDOVER, and others. 

Originals Men's Gazelle Lace-up Sneaker

by Adidas

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adidas Gazelle

It should come as no surprise to see adidas reappear on this list, given the brand's history and expertise in footwear. Although the adidas Gazelle often gets measured against its Samba counterpart, it deserves all the praise it receives as a standalone staple. Upon making its debut in the '60s, the adidas low-tops immediately struck a chord with soccer players before moving on to everyone else. 

Characteristic traits of the shoe are its streamlined silhouette, supple suede base, and distinctive three-stripe logo on the sides. It has a minimalistic charm artists find endearing, helping it evolve into a canvas for creative expression. Sean Wotherspoon did a number on the shoe back in April 2023, covering the upper in corduroy featuring colorful doodles. Looking for something higher up the luxury ladder? Gucci adds a fashionable flair to the shoe by applying its signature monogram pattern across four distinct color variations.

Men's Replica Sneakers

by Maison Margiela

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Maison Margiela Replica

Maison Margiela's Replica sneakers hold a unique place on this list for various reasons. Unlike the other shoes featured here, the Replica sneakers come from a prestigious fashion house instead of a footwear brand and are the only ones with no obvious ties to sports. The shoes are a high-end variation of a GAT (German Army Trainer) — an interpretative take on shoes worn by German soldiers in the '80s. Although brands like Puma and adidas offer their own variations of the military shoe, this iteration by Maison Margiela sent this style soaring into the style stratosphere.

The label applies the same care and craftsmanship to its shoes as it does to all other pieces in its historical archive. Maison Margiela's retro runners undergo an aging and distressing process to achieve a worn-in vintage aesthetic. A hit among fashion enthusiasts, celebrities, musicians, and athletes, they're one of the most popular sneakers to ever hit the market. 

Shoes That Stand the Test of Time

The impact these retro sneakers have on society reaches beyond the realm of footwear. Each has transcended its utilitarian origins to become a symbol of style and self-expression. Regardless of how many shoe styles enter the market each year, the shoes on this list will continue to stand the test of time and be the springboard from which all others launch.

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