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High Top Leather Sneakers – Five Plus One

Five Plus One is our weekly series of buyer’s guides. We pick a specific category and dig up five great options along with one that’s a little outside the norm.


I’ll be the first to admit that I’d wear heavy duty boots everyday if I could, but that simply isn’t feasible. Some days call for dressier shoes, while others call for sandals. And when you’re looking for a middle ground, some days call for this week’s focus: the high top sneaker. They’re simple and casual, but with a bit off added ankle support and warmth.

1) Gustin: High Top in Black/Black

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Gustin has come a long way from their simple raw denim days on Kickstarter, and one of their most attractive new offerings is their High Top Sneaker. The design is very understated but that’s what many of us want in a pair of sneakers. This blacked-out model’s made from a soft, black leather and is stitched to a black Margom sole, with nine eyelets from toe to ankle.

Available for $169 from Gustin.

2) P.F. Flyers for Todd Snyder: Rambler Hi in Saddle

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P.F. Flyers makes some of the best entry level sneakers on the market, but most of them are made from canvas. Luckily, their collaborations with Todd Snyder are constructed from leather, although the price is a bit higher. Their Rambler Hi in Saddle is made from a medium brown leather with a lambskin lining, and is attached to a contrasting white sole. Each pair is finished with flat waxed laces for a cleaner look than traditional, unwaxed laces.

Available for $160 from PF Flyers.

3) Maison Margiela: High Top GATs in Black

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Germany Army Trainers are among history’s most popular sneaker patterns, but this reinterpretation by Maison Margiela is quite unlike the original. The High Top GATs are several inches taller than the standard issue, which required the heel pattern to be modified. In addition, the heel piece and side embellishment are made from contrasting suede, but were made from smooth leather on the original. And that makes these some of the most interesting high tops on the market.

Available for $490 from Totokaelo.

4) Common Projects: Tournament High in Tobacco Suede

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Common Projects are most well known for their Achilles line of sneakers, but that shouldn’t take anything away from their Tournament Highs. Designed to look like traditional tennis shoes, the Tournament Highs are arguably the most understated of all of Common Projects high top sneakers. They’re shown here in tobacco suede with tan stitching, nickel eyelets, white sole, and Common Project’s famous ID number on the heel.

Available for $314 from Haven.

5) Rancourt: Court Classic High in Navy

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Rancourt’s Court Classic High is one of the newest additions to Rancourt’s line of footwear, and it’s a winner. The pattern features clean lines, a very narrow ankle opening, and minimal stitching throughout. It’s lined with Horween horsehide and features Vibram’s Strighton outsole, which is their closest thing they make to a simple sneaker cup sole. A range of colors are available, although the navy is among the most striking.

Available for $290 from Rancourt.

Plus One – Buttero: High Top Slip On in Army Green

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Buttero’s High Top Slip On is one part Chelsea boot and one part hi-top, but the horizontally stitched cup sole definitely puts these shoes firmly in the sneaker category. The pattern on the upper is pretty standard as far as Chelsea boots go, with elastic side panels on both sides and a pull-tab on the back, and this pair comes in an Army Green suede with a contrasting tan lining, giving them a distinctive military look.

Available for $380 from Buttero.