The 25 Best Sneakers of the Past 25 Years

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The battle between adidas and Nike over PrimeKnit and Flyknit will have to play out in the courts, but the fact that Nike made their shoe known first is incontrovertible. The Flyknit Trainer is the most well-known silhouette, seeing that it was repurposed for the mass-market Flyknit One, but the Flyknit Racer, which utilized the same upper as Nike's Olympic track spikes, is the real prize. As of now, the whole concept of knit uppers is in its infancy, yet this design will remain a powerful one for more than just its timeliness.

The balance between high- and low-tech has always been something of an uneasy one in skateboarding, with prehistoric classics like the Vans Era sharing shelf space (in both closets and stores) with various overbuilt successors. In recent years there's been something of a detente thanks to a whole new category - sleek shoes that evoked the former despite being fully advanced. Shoes like the Converse KA-ONE, the adidas Lucas, and the Nike Eric Koston 1. The Bruin-like upper is a work of near-seamless minimalist beauty, and the slim midsole conceals a thick Lunarlon insole. There's a sequel dropping shortly, but it's hard to improve on something so well done.

The Nike LeBron line took a drastic turn in 2009, as new designer Jason Petrie was able to incorporate Flywire as well as an all-new 360 Air sole. The result, the LeBron 7, was almost a homage to the classic Air Jordan XI, made even more apparent in a black and red "tribute" edition. The following year's model, the LeBron 8, was where the new aesthetic really took off. Best evidenced in the "Pre-Heat" South Beach colorway, the LeBron 8 mixed elegance and brute force in a way unseen since Sir Charles was tearing rims up in Phoenix.

As DJ Clark Kent has said, the Air Yeezy (and its even more-hyped successor) isn't a performance shoe, it's a performer's shoe. But at this stage, that seems like a more and more irrelevant distinction. Sports and entertainment seem to edge ever closer, and someone who performs as much as Kanye can certainly be considered some type of athlete. But it's the shoe that matters here, and the Yeezy, even with the easily recognizable Air Jordan III sole tooling, was something completely new. Even separated from the considerable Kanye cult of personality, this was a design that could (and did) hold its own.

Of all the athletes who get to work on signature product, none may be as involved as Kobe Bryant, This is both a gift and a curse to the designers, who - while they get plenty of input - might get a 3 a.m. phone call about why an outsole wasn't made a millimeter lower. For his fourth signature shoe from Nike, Bryant wanted designer Eric Avar to come up with something closer to a soccer boot, far lower than he'd worn in the past. And while the IV wasn't a true lowtop - not nearly as much as the shoes that would follow - it set a whole new standard for basketball shoes.

By 2007, high-tech had reached a high water mark. Basketball shoes and running shoes seemed to be on the brink of Skynet-like self-awareness, and advanced degrees were required to interpret the latest technological advances. Skate shoes had maxed out even earlier, at the beginning of the decade, with bloated models like the Osiris D3. So the Supra Skytop, which melded a traditional vulc sole with an exaggerated basketball-influenced hightop upper, was actually a breath of fresh air. Ironically, it came in the form of a signature shoe for Chad Muska, whose CM901 with Circa was in more of the D3 vein. Thankfully, people can change.

This might be fudging the whole "new models only" rule a bit, but the Spizike - built from parts of every Air Jordan that Mars Blackmon ever endorsed - is an exception to a whole bunch of rules. Like the idea of a Frankenstein sneaker creation being an unmitigated horror. The Spizike revels in its excess, and while Air Jordan traditionalists may cringe at the idea of parts of their favorites being utilized in such a manner, the sneaker proved so popular that an intended one-time tribute became a line mainstay.

Utilizing the then-somewhat-new Free sole technology on a trail shoe may have seemed counter-intuitive, but Nike has made a hell of a lot of money over the years by being exactly that. Not that the Free Trail 5.0 was some kind of monster at retail, but its very existence was what was important. Basketball shoes were becoming increasingly high-tech and complex (see the Air Jordan XX) and a basic trail running shoe with a perforated upper and decoupled sole represented a literal breath of fresh air. Compare the Free Trail 5.0 to many other sneakers of its era, and see which held up better.

How many basketball sneakers are still lusted after for their pure performance capabilities nearly a decade after their initial release? Not many. The Zoom Huarache 2K4, which possibly would have been Kobe Bryant's first signature shoe if it weren't for that Colorado incident, still has its adherents. The simple Velcro strap is a piece of proprioceptic wonder, and the combination of Zoom Air and a carbon fiber springplate is always welcome. Simpler is still better.

LeBron James was on board, and the entire Nike basketball design crew - led by Tinker Hatfield - was on call. Of all the shoes designed in Nike's storied history, this would have been the one to be a fly on the wall for the process. The Air Zoom Generation - no LeBron name for this one - took cues from his infamous Hummer, and was a high-tech marvel under an aggressive (if somewhat traditional) skin. Hard to believe it's been 10 years.

Before injuries robbed him of his explosiveness, Tracy McGrady was the absolute truth. He may have even temporarily been a better player than adidas teammate Kobe Bryant (although Kobe had started winning titles, while Tracy never could get out of the first round). What's undisputed is McGrady's adidas were far better looking than Kobe's Audi-designed toasters, stripping the original's revamped shelltoe to just a suggestion, provided by TPU strips. The stripes were embossed, the cut aggressive, and T-Mac was on top of his game.

The early '00s were a weird time for performance basketball sneakers - Mike was retired (again) and LeBron James was still whiling away the time in high school. Meanwhile, Allen Iverson's signature line was sort of all over the place, going from the Hexalite-cushioned Question to the all-new DMX-infused Answer. The ultimate Iverson shoe, it seemed, would simply emphasize his greatest trait - quickness. The Answer IV did exactly that, in a way that no Iverson shoe before or since could match. The zip-up shroud provided its streamlined design, and the whole look was based around motion and speed. A historic shoe.

Honestly, the original Nike Presto is the only sneaker that should ever show up under the #kicksonaplane hashtag. The proto-minimalist runner came in T-shirt sizes (XS to XXL) and provided T-shirt like comfort, with a decidedly stretchy upper and just enough lacing to keep them on. More a pre- or apres-performance shoe, the Presto invented a whole new category.

Last shot didn't mean last Jordan, but the Ferrari Maranello inspired Air Jordan XIV still represented a bit of finality - the last Air Jordan Michael Jordan would wear as a member of the Chicago Bulls. He broke them out far earlier than he'd normally debut a game shoe - the XIII was still releasing - and probably caused a few fits at Nike HQ, but no one ever told MJ what to do. And besides, the sleek sneaker, what with its suede toe, sculpted air vents and Ferrari-like badging was still going to look fresh no matter how long it took to release.

What do you do when the underpinnings of a shoe get too techy for the average consumer? If you're Eric Avar, you cover up all of your carefully laid-out detailing with a shroud. Hey, engine builders don't expect their work to be visible at all times, either. Gary Payton's signature shoe in all but name, the Zoom Flight 98 aka "The Glove" showed that it was possible to create a highly functional shoe, yet still present it in a clean package. Sneaker design would drift away from this ideal, only to come back full circle over a decade later.

Nike's Zoom Air cushioning wasn't brand-new for 1997 - it had appeared in 1995's Zoom Flight basketball shoe, and previously as "Tensile Air" in the LWP series. The Spiridon, however, a primarily mesh running shoe with major hits of 3M and a foil Swoosh, gave the technology an all-new showcase. And Air Max had a serious competitor, right in its own family.

In a sense, much of the Reebok Question's aesthetic was borrowed: Ghilly lace loops had been used on the Air Max and Air Jordan, and the giant Hexalite "windows" harkened to Air Max as well. But the all-leather kicks with the suede or pearlized leather toes were the newest design for the newest superstar, Philadelphia 76ers rookie Allen Iverson. And when the rook crossed up none other than Michael Jordan himself while wearing his blue-tipped pair, the world took notice. Of the player AND the shoes.

Sergio Lozano's 1995 Air Max design was one of the boldest out of Beaverton since Tinker Hatfield's original Air Max of 1987. Inspired by the human body, the layered upper led right into the all-new, full-length Air Max sole. And like the body, the whole unit worked as one. Every Air Max runner since has aspired to this.

Sneaker designers have been looking to do away with laces for years, so Reebok's Insta Pump Fury was quite the sensation when it dropped in 1994. The ultimate realization of the then five-year-old Pump technology, the Pump Fury also made do with a radically reduced midsole, thanks to the GraphLight plate, Hexalite cushioning, and a fully synthetic upper. The aesthetics are still futuristic.

It's hard to say whether the University of Michigan's Fab Five actually had MORE cultural significance and influence than Michael Jordan (actually it isn't - they didn't), but the fact is that people who weren't born when Chris Webber and company were in Ann Arbor still seek to sport their look. Or at least their sneakers. One of the models most associated with the Fab Five is 1993's Nike Air Force Max, which was simultaneously worn in the NBA by Charles Barkley. Imagined by the then-head designer of Nike's ACG line, it was the ultimate rugged and raw basketball sneaker of the early '90s.

A good designer isn't afraid to borrow from themself, and Tinker Hatfield did exactly that with the Air Jordan VII. Taking cues from the previous year's Huarache line, Hatfield mixed in some African influences, and gave the upper a bit more structure. The result was both lightweight and elegant, a perfect continuation of the Air Jordan pedigree.

Tinker Hatfield's creations take up many places on this list, and would take up many more if it weren't for the one year, one shoe constraint. Inspired in equal parts by traditional Mexican sandals and waterski equipment, he produced a sleek, lightweight neoprene and leather running shoe which also borrowed the sandal's name - Huarache.

The Air Jordan V, inspired in part by the World War II P-51 Mustang fighter plane, took the line off in a whole new direction and laid the groundwork for the next decade of basketball shoes. An assymmetrical ankle collar provided support only where it was needed, while a reflective 3M tongue provided untold amounts of on- and off-court flash. The grip was traditional herringbone, presented in untraditional clear rubber. Nearly 25 years on, these still look new.

Believe the hype, it's a sequel. The Air Jordan IV kept the same basic 3/4 cut as its predecessor, adding mesh panels and plastic wings for reduced weight and added ventilation and support. The speckled midsoles of the white "Do The Right Thing" version would become the stuff of sneaker legend, and the multiple lacing options gave heads plenty of ways to express themselves.

The best sneaker ever? Perhaps. So there can be no doubt that the Tinker Hatfield designed classic was the best sneaker of 1988. Not that there wasn't some tough competition, but the first Air Jordan to feature Visible Air and elephant print was on a whole different level. Equally respected on and off the court, the third Air Jordan established the mystique for good.