Expert Advice

Best Retro Sneakers to Add to Your Rotation Right Now

Aug 19, 2025

The classics never go out of style. The best retro sneakers are timeless, adaptable and iconic. From Chuck Taylors to the latest retro Air Jordans, here's a look at the old school kicks you need for your collection.

Nike Air Jordan Series: A Legendary Heritage

The first Air Jordans were released back in 1985. The most recent model — the Air Jordan 40 — dropped 40 years later, in the summer of 2025. The Air Jordan line is one of history's most influential and long-lasting sneaker series, encompassing a string of classic silhouettes. This gives Jordan Brand one of the biggest collections of retro shoe models to play with, and The House That Mike Built does not disappoint. Every year, we see coveted retro Air Jordan releases. True to form, we've already seen some of the best retro sneakers of 2025 dropped by Brand Jordan.

Air Jordan 4 Retro "Rare Air"

Air Jordan 4 Retro "Rare Air"

"Rare Air" is Jordan Brand's tribute to when those near-mythical misfit samples, production errors and unreleased colorways occasionally sneak out into the real world. The Jordan 4 Retro Rare Air is a fresh contribution to the theme. A black leather and suede upper is embellished with hits of blue, red, and grey. AJ 4 design staples like the visible Air unit in the heel are combined with special edition features like removable tongue patches.

Air Jordan 4 Retro "Pizza"

Another 2025 release, the Jordan 4 Retro Pizza, dropped exclusively in grade school (GS) sizes. The AJ 4 silhouette gets a sesame nubuck and suede upper with black, red and white accents. Pizza-box packaging added a playful note to the presentation at launch. The AJ 4 Pizza stands out as a good example of the Swoosh's proven ability to find fresh colorways for some of its best retro sneakers.

Air Jordan 5 Retro OG "Grape"

Air Jordan 5 Retro OG "Grape"

A pretty faithful OG reissue, the Jordan 5 Retro Grape that dropped this summer is about as close to the original release as you can get. The OG was made famous by Will Smith as the Fresh Prince of Bel-Air when it originally launched in the '90s. The "Grape" release had crisp white leather uppers, grape ice hits on the midsole and tongue and new emerald on the AJ 5 shark teeth (the model's defining design feature). 

Nike Dunk Low: Classic Performance + Modern Twist

The Nike Dunk Low was a classic '80s basketball shoe reimagined for skateboarders in the 2000s (as the Nike Dunk SB). The low-profile version of the shoe (mid and high-tops are also available) sits alongside Air Force Ones as Nike's most iconic retro, low silhouettes. 

 

The Dunk Low turned 40 in 2025, and the Swoosh has kept the streetwear staple evergreen with a string of new and reissued colorways, most notably some fresh takes on the classic black-and-white "Panda."

 

Changes in shoe manufacturing tech mean that retro editions often differ slightly from their OG counterparts. If you put a 2025 Dunk next to one of its '80s cousins, you'd soon notice how sneakers have changed over the years (most notably in materials used). Modern retro shoes are typically only old-school in styling. They're made using modern techniques and materials (for the most part) and generally fit true to size in common with today's sizing standards. 

 

Watch out for model-specific issues with sizing. For example, AJ 5s can be a little tight on wide feet, with some choosing to go half a size up from TTS.

Reebok Club C 85 "White/Grey" Women's Shoe

Reebok Club C: Timeless Tennis Style

What Nike terms "retro" becomes "vintage" over at Reebok. The Reebok Club C 85 Vintage is a modern reissue of a classic '80s tennis shoe. If you're looking for that all-white, lace-up, low-pro retro style, you're looking for the Reebok Club C.

 

Incidentally, terms like "retro," "reissue" and "vintage" are sometimes synonyms and sometimes signify very different things in the sneakersphere. For example, over at Nike, "retro" basically signifies a reissued model. That's what Reebok calls "vintage" for the Club C. For some sneakerheads, "retro" is a type of reissue. For example, a release that very specifically seeks to mimic an OG colorway.  When Vans dubs a release a "reissue," they're talking about what Nike would call a "retro" release.

 

Confused? Don't be. Your local sneaker store can quickly clarify if those retro kicks you're eyeing are old school or just old.

Converse Chuck Taylor All Star

Converse Chuck Taylor All Star 1970: Icon Redefined

Some shoes are collector's items because of their rarity, like original Air Jordan 1 Low 1985 colorways. Or because they have limited edition scarcity. And some are simply iconic. The Converse Chuck Taylor All Star is one of those all-time classic shoes. It's not rare, but no sneaker collection is complete without a pair. 

 

Chuck 70s are built with thicker canvas, better support and generally better durability — your feet will thank you for knowing the difference between 70s and standard All Stars.

New Balance 1906

New Balance 1906: Everyday Classic

Thick soles, neutral colorways, outstanding comfort and throwback Y2K vibes: that's the recipe for a perfect Dad shoe. And there is no more perfect Dad shoe than the New Balance 1906. It's routinely recommended as one of the best men's retro sneakers (though let's not pretend women aren't also enjoying this chunky soled classic).

Build Your Retro Sneaker Collection Today

Check out what's new in the old school: Shop the Hibbett collection of retro sneakers online or via the Hibbett mobile app. Or stop by your local Hibbett store today.

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