The 20 Greatest Sneakers of All Time (And Where to Buy Them)

Yep, we're crazy to do this; let's just get that right out of the way. Any "all-time" list is going to be highly personal and prime for debate, especially when it comes to footwear. One guy's must-have style is an easy pass for another. What we've collected here are a handful of perennials, a few statement pieces and some standout one-offs. Although they won't immediately fit with everyone's personal style, you really can't go wrong with any of them, trust us—they truly are the epitome of classic.

Air Force 1 Now in its 30th year, the Air Force 1 deserves a place on any all-time-greatest list. Though you can still cop it in classic iterations of all-white and all-black, the latest line incorporates new profiles (in the Air Force 1 Downtown) and models with updated, more comfortable Lunar soles. Classic White $90 Classic Black $90 Air Force 1 Downtown $135 Air Force 1 Lunar Fuse Leather $125

adidas Superstar Made famous by Run-DMC, the hip-hop classic never goes out of style and has inspired numerous variations. A recent mid-top remix is the Pro Model II All Black Adidas Originals X Big Sean, capitalizing on the brand's continued support from stylish MC's. Original Superstar 2.0 $70 adidas Originals X Big Sean Pro Model II 'All Black' $160

Jack Purcell Converse may have purchased the trademark rights to the Jack Purcell sneaker in the '70s, but in the last ten years it's seen a resurgence as the understated complement to the more well-known All-Stars. With its signature smile toe, it's an easy win for any season. Jack Purcell $60

Nike Air Jordan III All sneaker lists deserve at least one spot for His Airness, but choosing just one is often the hardest part. The III is an all-time fan favorite that is regularly re-released in small quantities and is almost always up for auction on eBay. For those unwilling to wait, try your hand at Nike ID customization on a pair of Spizike Jordans and keep your fingers crossed for the next retro. Nike Air Jordan Spizike ID $210

Vans Slip-On These are an absolute summer must-have and verified classic after Spicoli (Sean Penn) sported them in Fast Times at Ridgemont High. Although new colors are released every year, you can't go wrong with the OG checkerboard. Checkerboard Slip-On $47

ASICS GEL Lyte III First released in 1991, the Gel Lyte III is best known for its split tongue. In recent years the shoe has become a go-to canvas for top collaborations and a fantastic alternative for fashion-forward fans looking to move on from Nike or Adidas. Asics Gel Lyte III $100

Adidas Stan Smith > Common Projects The tennis shoe is a total classic, and although it's currently unavailable, Adidas is set to bring it back in a 2014 model. In the meantime, fans of the shoe's simplicity should check out Common Projects' version; though pricer then their inspiration, their sleek, versatile style is liable to turn even the most casual shopper into a true sneakerhead. Common Projects $400

Air Tech Challenge II The Andre Agassi classic is in constant pursuit by deadstock sneakerheads and recently returned for the US Open in a special 21 Mercer black-and-blue colorway. This latest version is still hard to find; tennis fans should try eBay. Nike Air Tech Challenge II $290

New Balance 998 $160 There have been many New Balances worth a purchase, and if Steve Jobs is any indication, they can make for the ideal daily uniform. A recent favorite is the 998 collaboration with J.Crew. A style originally only available in Japan, you can now order them direct from the beloved mall chain. New Balance 998 $160

Gourmet "Jordan Inspired" In 2008, shoe company Gourment released this grown-up style inspired by Jordan classics, causing many to wonder if they would be sued out of existence. Though several of those original models have been discontinued (or ceased-and-desisted?), the brand continues to put out head-turning alternatives, including the latest Nove 2 L in full grain leather. Gourmet Nove 2 L $110

La Gear, LA Lights In the '90s, no middle school routine was complete without borrowing mom's cellphone and strapping on some LA Lights. Who knew these were still available? It takes a real man—or a lot of molly—to pull these off today, but they'll look great on your next trip to Electric Zoo. La Lights $100

Air Max 1 A.P.C. Any list of classics would be incomplete without Nike's most versatile, style-forward silhouette, the Air Max 1. Although the shoe has come in numerous iterations, a recent favorite was a collaboration with A.P.C. that featured street-ready gum soles and a leather tongue and trim. Although this exact style may be hard to track down, fans of the simple look should check NikeID, where you can customize a shoe that's almost as fresh and will still go with everything. Air Max 1 A.P.C. $120 Sold Out Air Max ID $150

Puma Disc Although most of us remember Reebok Pumps as the most unique sneaker-tech style of the '90s, hip-hop heads couldn't get enough of the Puma Disc. The look has made a mini-comeback among today's sneakerheads thanks to Ronnie Fieg and his collaborations available at KITH. Puma Disc Blaze Lite $130

Nike Free Run 2 > Roshe The Nike Run's innovative free sole brought both flexibility and fashion to running. In 2011, The Run+ 2 became the must-have style in the menswear scene. It continues to be a favorite thanks to regular color updates and new material mixes from Nike Sportswear. For something even more on time, try the new Roshe run. Barely a year old and constantly being mixed in different color combinations, it looks great on the track or the street. Nike Free Run 2 Nike Roshe Run $70

Puma Clyde Classic You can't go wrong with something so right: Available in a variety of colors to complement any look, this was the original signature basketball shoe; unveiled in 1973, it's still going strong. Puma Clyde Leather $60

Nike HTM Flyknits Nike launched its most innovative product in years with the lightweight, formfitting Flyknit HTM's. Available in super-limited quantities, the style is almost impossible to come by. Good thing the brand offers a variety of evolutions of the technology, including our favorite, the Flyknit Chukka. Nike Flyknit Chukka $170

New Balance 420 While maybe not as special or fever-inducing to sneaker-heads as the 998, the 420 is one of the most easy-to-wear running shoes available today. With colorways that harken to the '70s plus an extreme low profile, these look especially good with a rolled-up pant leg. New Balance 420 $65

Kanye West for Louis Vuitton Don's > Filling Pieces They may not be as well-known as Kanye West's Yeezy's, but the hip-hop icon's Louis Vuitton collection was both unexpected and highly sought after. Almost as hard to find but certainly more available is the Filling Pieces low-top trainer. These clean modern classics will still turn heads and can be found for about a third of the Ye's original LV retail. Filling Pieces Low-Top Trainer $230

Vans Half Cab The Half Cab is one of the most iconic skate styles that's still being produced; it's inspired almost every modern skate shoe. Today, the best versions can be found at New York's DQM for Vans store in SoHo, where they've been modernized with a more grown-up aesthetic: The Vans Vault X WTAPS OG Chukka is an worth immediate purchase. Vans Half Cab $60

Nike Air More Uptempo "Scottie Pippin"This list needed at least one more basketball shoe to round it out, but narrowing it down was damn near impossible. The odern Lebrons? The culty Foamposites? Instead, we went with the Nike Air More Uptempo. Screaming 'Air' on the sides and worn during the Bulls' heyday, these were almost as iconic as Jordans of the same era. You can still find them on eBay for $200-$400, but for a modern alternative, try the Hyperdunk. Not as flashy as the OG Uptempo, it's one of the lightest basketball shoes available today. Nike Hyperdunk $140