Before diving into any list of the best men’s high-top sneakers, a high-top history lesson is in order. Back in the early 1900s, the nascent sport of basketball had players running up and down the court in all-leather basketball shoes. Imagine your great-great-grandpa was out there dropping dimes in derbies, basically. In 1917, Converse showed up with the first pair of made-for-the-court kicks, pairing a vulcanized rubber sole with light-but-strong canvas upper that covered the ankle to keep the shoe locked in place. (Now imagine your great-great-grandpa crossing up some guy in short-shorts and a shorter fade.) It was the beginning of our high-top sneaker obsession, and the starter pistol shot that saw high tops become a footwear frontier pushing the boundaries of both shoe tech and style.
Any list of the best men’s sneakers today—hell, the best men’s shoes, period—is still packed with a few high-top O.G.’s from the likes of Converse, Nike, and Adidas. They’re joined, of course, by fresh takes on the high-top sneaker: if you’re in the market, you can lace up a pair of high-tops with everything from skate cred to trail-crushing tech to designer DNA.
The Best High-Top Sneakers for Men Shopping Guide
What should I wear with high-top sneakers?
We didn’t specifically mention high-tops in our new do’s and don’ts for dressing right now, though a few of our guidelines can apply. We like sneakers a bit better when they’ve got a little wear. We like them less, lately, with a suit. As ever, there’s no such thing as a rule in menswear—there are only opinions and vibes. Here are some of ours when it comes to styling the best high top sneakers in your fits:
- Not to intentionally coin a farmers’ almanac-style mnemonic, but fall and spring tend to be when high tops sing. In most regions, winter calls for boots, and summer is shorts season. Speaking of…
- The shorts-and-high-tops combo is an advanced maneuver, but not impossible. We’d lace up a pair of high tops with some nicer mesh basketball-style shorts or (no lie) some retro jorts and see where that takes you.
- Visible socks, always. (Sorry, no-shows.) Even the best men’s high-top sneakers need a partner. We’ve got our favorite men’s socks here if you’re looking.
- When in doubt: Converse Chucks. They work with anything, anytime.* (*Some limits apply; your mileage may vary; don’t show up at a funeral or job interview and point at us.)
The Perennial All-Star High Tops
If a High Top Hall of Fame Museum existed, there’d be a 40-foot Converse Chuck Taylor sneaker out front, visible from the highway. Explaining why the hoops-born high top icon works is like explaining how a color looks—but fine, we’ll try. The shape is flawless, the slim canvas upper ensures the ankle syncs up flawlessly with any type of pants, the price is right, and the simplicity allows for infinite variations. (You’d need an airplane hangar to stash every Converse colorway.) Not to mention the Chucks are synonymous with some of culture’s most stylish dressers. We tend to prefer the Chuck 70 high top over the Converse Chuck Taylor All-Star high top for its thicker sole, better insole cushioning, beefier 12-oz. canvas, and slightly less-scrunched toe box—though style-wise, you can’t go wrong with either version.
The Downright Legendary High-Tops
The 100-plus-year timeline of high top sneakers can be best broken down in two parts: Before Jordans and Post-Jordans. The Nike Air Jordan I is, of course, Year Zero. Some 48 years since it went on sale to the public, the eldest AJ high top isn’t the best on-court Jordan. (That honor probably goes to the Jordan XIV.) It doesn’t have the most iconic features. (Our top contenders: the III’s elephant print, the IV’s cage, or the XI’s patent leather.) Yet the Nike Air Jordan I is DaVinci’s Vitruvian Man for high tops—the proportions (that Swoosh size!), the paneling, the flat tongue, the instantly identifiable silhouette conspire to create what we now think of as the platonic high top. And for nearly five decades, it’s looked as good off the court as it did on MJ’s feet.
The Skate-Ready High-Tops
Not too many skater-approved sneakers come in high top models, but that only adds to the Vans Sk8 Hi’s legendary status—and possibly explains why it’s become so beloved even by those of us who can’t hit a kickflip. The sneaker’s contrast stitching is as identifiable as Vans legendary Sidestripe logo, though it’s the combo of simplicity, shape, and infinite colorways that helps them railslide into any footwear rotation with ease. (Maybe this is our OCD talking, but even the dreaded bird’s-eye view looks great when you lace up Sk8 Hi’s.)
The Rebooted High-Tops
In 2020, NYC-based streetwear brand Aimé Leon Dore rebooted the forgotten New Balance 550 low-top as a brand-exclusive model, which saw it reselling for multiples of the sticker price. Then NB relaunched the model to everyone, and it’s enjoyed a steep rise to street-style ubiquity among guys who sip lattes while shopping for $200 double-knee pants. If that’s all gibberish to you, great. All you need to know is that the 550’s wild ride on the hype rollercoaster led to the rebirth of the New Balance 650 high top, which might just be a better shoe anyways. Same brick-like aerodynamics, thick leather overlays, and Seinfeldian style—but where the 550 cuts off, the 650 presses onwards (and stands out) with a padded collar, extra eyelets, and a much less complicated backstory.
The All-Terrain High-Tops
What, you thought the best high top sneakers all had to be sports inspired? In an age where trail-ready Salomons have attained sneaker nirvana and gorpcore style has fully permeated menswear, don’t sleep on the SUV of sneakers, the Adidas Terrex Swift R3. Like an AMG G-Wagen, they sacrifice nothing: you get lightweight sneaker DNA (breathable mesh upper, speed lacing, EVA midsole) paired with all-conditions brawn (rock-solid collar, GORE-Tex membrane, Continental™ Rubber outsole). Point being, the Terrex Swift R3 will hold its own on a trail, but looks equally cool on concrete.
The High-Fashion High-Tops
One look at the Rick Owens Geobaskets, from the dark lord of fashion, and you either get it or you don’t. To those of you who do, welcome. These big steppers, launched 14 years ago, are arguably the definitive high-fashion high-top. It’s all in the goblin proportions: a rubber outsole prepped for the apocalypse, a tongue that can almost block out the sun. No high top dominates a field of view like these. We could also go on about how, unlike a lot of designer sneakers, the Geobaskets wear in beautifully thanks to buttery calfskin and suede (in the lining, too). But you’ll discover the staying power—and enjoy plenty of in-the-know jealous stares—soon enough.