<p>Which brings us to the ever-present high-top conundrum: how to wear them. If you’ve ever been scarred by an adult man in a pair of misplaced Jordans, we see and we hear you. But we’re also here to help. Sure, it’s true that some styles of pants work better with <a href=”https://www.esquire.com/style/mens-fashion/g63588431/best-low-profile-sneakers/” target=”_blank”>low-tops</a> than highs, notably <a href=”https://www.esquire.com/style/mens-fashion/a64634932/how-to-style-wide-leg-pants/” target=”_blank”>anything looser and longer</a>. So if you’re wearing your <a href=”https://www.esquire.com/style/mens-fashion/g1885/10-white-sneakers-to-wear-right-now-071514/” target=”_blank”>trustiest high-tops</a>, you can play it safe and opt for something with a more tapered silhouette or something that’s cropped, or go baggy and let it pool around ‘am. As a general rule of thumb, we advise skipping high-tops with shorts. It cuts the line of an outfit off completely. (Unless, of course, that’s what you were going for. In which case, as you were.)</p><p>As for what to wear up top? The world’s your oyster. Pair a tee and a <a href=”https://www.esquire.com/style/mens-fashion/g64338787/best-mens-jean-jackets/” target=”_blank”>trucker jacket</a> with some on-the-shorter-side jeans. Throw a <a href=”https://www.esquire.com/style/mens-fashion/g3357/best-hoodies-men/” target=”_blank”>hoodie</a> on top of those slim track pants. It’s all fair game. For that final question—which pairs of high tops are our favorite—just keep reading.</p>” data-next-head/>
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PF flyers
Most Classic High-Tops
Converse Chuck 70 Canvas
Pros
Classic style
Cons
Virtually no support
If you’re afraid of looking too youthful in a pair of Converse, we suggest Chuck 70s. They’re a bit more premium than the Taylors and don’t wear quite as flat or quite as cheap. Black canvas on a white sole is a classic. There are many iterations of the Chuck Taylor All Star, many of which are very good. But none of them—none!—beats the comfort and throwback charm of the Chuck 70.
Upper material
Premium canvas
Best Less-Than-$100 High-Tops
Vans SK8-Hi
Pros
Easiest to style
Cons
Will look beat-up quickly
An all-white SK8-Hi requires not that you be a skater, but that instead you honor these shoes with a great pair of pants to match. Say, something cropped and wide? Denim, even? These are the easiest high-tops to style, and we love them for that.
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Best All-Around High-Tops
Nike Blazer Mid ’77
Pros
Great leather option
Cons
Very popular
If you want a leather upper versus a more casual canvas, Nike Blazer Mids are our favorites. You can go for the classic black swoosh, but we also like the small hit of color (like this green or a blue) for something different. Wear them with your favorite light color denim and a fresh T-shirt.
Upper material
Leather, suede
Best High-Tops for the Office
Beckett Simonon Garcia High Top
Pros
Look luxe
Cons
Require more break-in time
Beckett Simonon’s high-tops are a more substantial, chunkier shoe that can easily be worn with a more tailored pair of slacks or dark denim. Great for the office, great for a date, great for just about anything.
Upper material
Leather, suede
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Best Old-School High-Tops
P.F. Flyers Center Hi Vintage
Pros
Lightweight
Cons
Not a ton of support
Now, if that old-school, lived-in high-top is what you are going for, there’s nothing more old-school than a P.F. Flyer. The lightweight canvas sneaker comes in black and white, with a few iterations of both. It’s designed for cool spring and summer outsidoor (non-active) activities.
Best ’80s High-Tops
PONY M-Pro High Sneakers i
Pros
Great hit of blue
Cons
Can be stiff on first few wears
PONY’s high-tops are also extremely ’80s. They have a bit more chunk than a Chuck but not as much as a Jordan. They’re sporty but not in a off-brand way. We love the personality the bright blue stripe gives, but there are more subtle colors, too.
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Easiest High-Tops
Veja V-15 High Tops
Pros
Great for cool summer days
Cons
On the pricier side
Veja’s high-tops are not as popular as the lows, but we’re making the case for ’em. These are just as comfy to wear, look put together enough for work, and have a more modern sillohoutte, for those not ready for the full retro approach.
Best Upgrade High-Tops
Greats The Royale 2.0 High
Pros
Look pricey
Cons
Sizes tend to sell out quickly
Greats makes these high-tops that look significantly more expensive than they are, and they feel that way, too. They’re fresh right out of the box, with a more supportive platform and hugged-in collar than some of the canvas options.
Upper material
Leather, suede
The Most Beloved High-Tops
Jordan Air Jordan 1
Pros
Always have fresh colorways
Cons
Jordans not for everyone
What is there to say about the Air Jordan 1 that we haven’t already said, and said again still? It’s definitely the most sneakerhead-y sneaker on this list, but we love a simple colorway (like this brown suede, or an all white) for keeping on trend but staying out of the hype cycle.
Upper material
Suede, leather
Most Luxe High-Tops
Zvelle RAY SNEAKER
Pros
Excellent materials and construction
Cons
Pricey
For high-tops that are an upgrade in more than just aesthetics, Zvelle’s leather sneakres are some of the best constructed shoes we’ve put our feet in. You can’t go wrong with the all-white version, but for something a little different, we’re partial to this cool navy leather.
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What to look for
If you’re venturing into high-tops for the first time, this is the best advice we can give: go shopping with your pants on. Like, go try on a bunch of sneakers with the pair of pants you’d imagine you’ll be wearing those sneakers with the most. High-tops are harder to style than low, and buying a pair that you have ensured looks great with your chosen pants means preventing eventual styling conundruums. Bring a trusted confidant with you, too.