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The Best High Top Sneakers of 2020: the Fresh, the Funky, the Fashionable

Not quite a boot but more than a regular sneaker, high tops have found themselves integrated into shoe culture over the last 50 years. Like most categories in men’s fashion, the pieces we wear today were first created with an actual purpose in mind. When it comes to high top sneakers, many were originally designed for sports that required ankle support and protection while others drew inspiration from classic boot styles.

One of the most iconic styles, the Chuck Taylor All Star, was born back in 1922 and went on to be a standard basketball shoe for nearly 40 years. The 1970’s produced a new era of skateboarding shoes, with Vans leading the charge and creating their iconic SK8-Hi that would influence new skate designs still to this day. The ‘80s, however, completely blew up the high top sneaker market, with new designs from brands like FILA, Reebok, British Knights, and most importantly, the introduction of the Nike Air Jordan.

Before we continue, jot this down: high tops make you look cool. The best high top sneakers of 2020 are a mixture of old and new, including:

  • Classic high top sneakers
  • Reissued retro high top sneakers
  • Modern high top basketball sneakers
  • Sustainably made high top sneakers
  • Lifestyle high top sneakers
  • Luxury high top sneakers

While some of these styles have been around for decades, others are more modern, designed by new faces to the sneaker community who create for fashion’s sake — which is cool too. Whether you’re looking for your next pair or are new to the game, here are our top 15 high top sneaker picks for 2020.


1. Greats Court High


Leading the list of the best high tops of 2020 is the Greats Court High, which we previously ranked “Best High Top Sneaker” in our best casual shoes line up. This shoe is everything you need in a high top. It’s made in Italy, has subtle and neutral tones and sits at a great price point, just over $200. This high top rivals those from designer brands, some even made in the same factory, coming in at well below half their prices. This truly is the best bang for your buck, especially when considering all they can match with.

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Image courtesy of Greats

2. Comme Des Garçons Play x Converse Chuck Taylor Hidden Heart High Top Sneaker


Most people have owned at least one pair of Converse Chuck Taylor high tops in their lifetime, but the collaboration sneaker with Comme Des Garçons is one of the greatest design variations to ever hit the market. This shoe continuously sells out after being restocked. Not only do CDG fans love it, but as sneakers go, the red logo adds a great pop of color to an otherwise plain shoe. Get this while it’s still available. Size down if you typically take a half size.

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Image courtesy of Nordstrom

3. Jordan 1 Mid Chicago Toe


This sneaker is just as legendary as the Air Man himself. Jordan 1’s are atop most sneakerhead’s lists as the number one dopest shoe of all time, especially in this colorway. The Jordan 1 Mid Chicago Toe was a reissue, released in April 2020 and is already selling for an average of 60% over MSRP on StockX with a high of $477. If you’re a collector, this is one you need to have. Earlier in 2020, a game-worn pair of this style sold for $560,000 at auction, breaking the previous sneaker record price of $437,500, also for a pair of Nikes.

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Image courtesy of StockX

4. American Rhino Lamu High Top Sneaker


Since 2016, American Rhino has been working to promote conservation land, wildlife and local communities in Kenya. What began as a way to spread awareness and thank donors turned into a well-rounded fashion lifestyle brand, with 95% of products manufactured in Kenya, helping to contribute to their local economies. The Lamu High Top Sneaker is made in Kenya and crafted from cruelty-free leather with a memory foam insole and a full rubber sole. They’re a perfect minimalist shoe for the everyday outfit and are also available in brown and green suede. A portion of all sales go to the American Rhino Foundation

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Image courtesy of American Rhino

5. Vans SK8-Hi


The Vans Sk8-Hi is one of the most iconic skate shoes, and arguably one of the most iconic high top sneakers, of all time. Since 1978, the Sk8-Hi has been protecting ankles and preventing injury one fall at a time. These shoes are made with the Vans-famous vulcanized rubber waffle sole for grip and shock absorbency while skating. Over time, this style has become a popular lifestyle shoe for casual and streetwear, collaborating with brands like Disney, the Simpsons and National Geographic, to name a few. The black suede is always a great color choice, but other hyper-popular colors include Racing Red, True White and Navy. These look awesome with a fresh pair of joggers.

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Image courtesy of Zappos

6. Christian Louboutin Louis Spikes High Top Sneaker


In case you were wondering, this is a sexy shoe. Christian Louboutin is best known for the trademark red-bottom sole on each shoe they design. But let’s give Loubie some props for making one of the best high top sneakers in the men’s designer world. Channeling that sweet spot between classy and sassy, doing both very well individually, this version of the Louis Spikes uses a flat pebbled leather in fennec (not fox leather) beige with a tonal stitch and gunmetal spikes covering the toe cap. These would look just as good dressed up with a beige or black suit as they would dressed down with a pair of destroyed denim and an oversized white tee.

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Image courtesy of Saks Fifth Avenue

7. Wolverine 1000 Mile Combat Tall


Hear me out — yes, this sneaker is on the cusp, maybe the wrong side, of being a boot but it’s still super cool. The Wolverine 1000 Mile Combat Tall is the ultra high top, combat-sole version of the classic sneaker bearing the same name. This is perfect for somebody who likes to “stomp” where they step, as it masterfully handles brick, cobblestone or any uneven ground. Wolverine sourced this unique leather, that has a metallic sheen incorporated into the royal blue color, from a tannery in Leeds, England Writing as somebody who owns this, they look fantastic with a pair of black jeans and anything white or grey.

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Image courtesy of Wolverine

8. Nike SB Zoom Blazer Mid Sashiko Sesame


Just dropped on but already 90% sold out, this Blazer Mid is my pick for the best high top sneaker of 2020. It may not be the biggest in hype, nor made in an iconic color scheme, but this shoe presents something fresh and culturally interesting. Sashiko is the Japanese technique of decorative reinforcement stitching; an artform of design. This shoe came in both beige and navy, but the beige boasts a beautiful contrast between the blue patchwork and stitching. If you cop these, try them out with a clean white top and bottom and toss on a blue cotton blazer — how fitting!

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Image courtesy of StockX

9. Supra Vaider High Top Sneaker


The Supra Vaider is one of the most popular high top skate shoes, and has been for years. The Vaider offers maximum ankle support, with a padded tongue, extended collar and ankle-height laces. The rubber sole is durable but flexible and the innersole is built with memory foam for all-day comfort on a board. As far as white sneakers go, this is also a pretty incredible silhouette that absolutely crushes any jogger or denim look between zero and ten on the grungy-fancy scale.

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Image courtesy of Zappos

10. TCG Hunter w/ Red Luxe Sole


The LA-born “cashletic” (casual + athletic) brand, TCG, wants to make sure that you’ve got gear that’ll work wherever, whenever you need it. The Hunter style is one of the most versatile high top sneakers from TCG’s lineup. This sneaker’s premium leather upper and off white outsole give neutrality to your look with a dash of couture from the red luxe sole. These would look just as good with your fall denim as they would with your tweed suit. The sky’s the limit with these classy looking high tops.

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Image courtesy of TCG

11. Puma x The Hundreds Performer Mid


Puma and The Hundreds team up to make one of the best high tops of 2020 in the form of Puma’s Performer Mid. Part of the “people over product” collab, this shoe takes us back to ‘90s street style and celebrates different cultural movements of the decade from preppy to jock to party crew. The orange and purple color scheme is a great pop of color for fall and breaks away from the monotony of neutrals throughout the week.

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Image courtesy of Puma

12. Puma Ralph Sampson Mid Sneakers


People are sleeping on Puma this year, and the Ralph Sampson Mid drop is proof. Ralph Sampson, for those who forgot, was the #1 overall pick in the NBA Draft of ‘83 and earned the Rookie of the Year Award in ‘84, the year before Jordan. The Ralph Sampson sneaker offers mid-height ankle support and a lightweight design for quickness on the court or wherever else you’re walking. This colorway of the Ralph Sampson is an ideal white high top sneaker with just a minimal, but bold touch of red. These have a true ‘80s vibe to them which is very hot right now.

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Image courtesy of Puma

13. Air Jordan 12 Retro Black University Gold


If you’re looking to go for bold, you need to look at the Air Jordan 12 Retro in Black University Gold. These high tops stick out from a crowd and look ultra-luxurious. This colorway was never released to the public but is available on StockX today and is one of the best selling Jordans of 2020. If these catch your eye, try them out with your favorite pair of black jeans and a black oversized sweater this fall.

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Image courtesy of StockX

14. Veja Nova High Top


If you can make a vegan product and have it look super cool, you do it. That’s exactly what Veja did here with their Nova high top sneaker. This is one of the best high tops of 2020 because of the brand’s attention to detail in crafting an eco-conscious shoe that looks as fashionable as it does, using organic cotton and wild rubber. The beige color is great for fall, but the black or white colorways are also great staples for an everyday sneaker. This type of style looks great with a pair of jeans or chinos and a cozy hoodie.

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Image courtesy of Veja

15. Vince Fynn High Top Sneaker


Basic black is never a bad thing, especially when you’re looking for your first pair of high tops. Vince makes the Fynn, which is one of the best minimal high top sneaker options for 2020. A leather upper in solid black sits on a white rubber sole to craft a sporty, clean look that complements any kind of style. If you need it to look polished, it’s got you covered. If you’re just kicking it for the weekend, these can take you from day to night in a breeze. Wear these with your favorite pair of dark jeans and your new leather jacket.

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Image courtesy of Nordstrom

BONUS: Nike MAG Back to the Future (2016)


High top sneaker goals here, the Nike MAG Back to the Future was dropped in 2016 as the real-life model of Marty McFly’s self-lacing shoes from Back to the Future Part II. This was a very limited release but can be found for auction on StockX in select sizes starting at a cool $40K. Do it. I dare you.

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Image courtesy of StockX

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