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Step Out in the Best Men’s High-Top Sneakers this Season for 2021

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Fall calls for something a little bit different, something a bit tougher and more versatile on the footwear front. Fall calls for high-tops. Specifically, it calls for quality sneakers that blend comfort and classic looks with durability and an added flair to take on chilly, rainy autumn weather. 

The best high-top sneakers blend classic looks with unbeatable style, the kind that you only get when shoes are built to last. These are an upgrade from your low-top summer sneakers, with the sort of durability that fits right in alongside your flannel shirt and your selvedge denim, both of which are fall style classics, too. And since the style is rooted in old-school performance (think of the first basketball shoes, for instance), well, high-top sneakers look great any way you slice it. The time is now to acquaint yourself with a casual pair of kicks you can rock this season and well beyond.

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Best Overall High-Top Sneakers: Converse Chuck Taylor All Star

High-top sneakers for men.
Converse / Converse

These shoes are an undeniable classic, the sort of sneakers that look good with pretty much anything and stand the test of time. Wear them with jeans or chinos and an Oxford shirt, then add a shawl cardigan for retro, office-friendly style.

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Best High-Top Sneakers for Throwback Style: Reebok Royal Hi2 Sneakers

Reebok sneakers for men.
Amazon

There’s just something about these sneakers that calls to mind the ’80s or the ’90s, which makes them a fashionable throwback option. Add in black jeans and a grey T-shirt or crewneck sweatshirt for style that really lets these sleek sneakers stand out.

Best High-Top Sneakers to Wear With Jeans: Levi’s Stanton Waxed Sneakers

Levi's sneakers for men.
Image used with permission by copyright holder

The thing with Levi’s is, the famed denim brand now make so much more than just jeans. Note these nubuck sneakers, with eye-catching detailing that pairs nicely with a slim pair of Levi’s jeans this season.

Best Canvas High-Top Sneakers: adidas Nizza RF Hi Shoes

Stylish sneakers for men.
Amazon

The sportswear experts at Adidas know a thing or two about making standout high-top sneakers. This canvas pair offers up an understated take on the classic “three stripes” design, all the better to wear casually with jeans this fall.

Most Sustainable High-Top Sneakers: Cariuma OCA High Sneakers

Sustainable sneakers for men.
Cariuma

Cariuma makes sustainability the name of the game with these sneakers, using ethical manufacturing practices that cut down on waste and utilize repurposed materials whenever possible. The result is a pair of timeless kicks you can feel great about wearing.

Best Investment-Level High-Top Sneakers: Tom Ford Black Cambridge Leather Sneakers

Luxurious leather sneakers for men.
MR. PORTER

If there’s a designer that can do it all when it comes to upgrading your essentials with everyday luxury in mind, it’s Tom Ford. Here, he takes the sporty high-top and turns it into something to be worn with a suit.

Other Sneakers We Love

TAFT Jack Sneakers

Leather high-top sneakers for men.
TAFT

Add some fall-ready design to your footwear rotation with these pleasing, super-cool mixed-media sneakers from TAFT. They’ve turned a suiting pattern into a cool accent for fresh leather kicks. Wear them to dressy dinner parties this season.

Nike Blazer Mid ’77 Sneakers

Nike sneakers for men.
Nordstrom

Nike turns back the clock with these cool-as-can-be, vintage-inspired kicks in a rich fall tone. Wear them with blue jeans and a grey henley for that added pop of fall color.

Vince Flynn High-Top Sneakers

Hight-top men's sneakers for fall.
Nordstrom

Take a minimal approach to your wardrobe with these crisply designed high-top sneakers. They can easily be teamed with tan chinos and a navy blazer for high-low office style.

Editors’ Recommendations

Beau Hayhoe
Beau Hayhoe
Former Digital Trends Contributor
Beau Hayhoe is a freelance men's style writer, consultant and PR pro based in Brooklyn. Beau's menswear and gear writing has…
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