Highsnobiety / Eva Al Desnudo

At the more formal end of the shoe spectrum, most of us have previously rocked the likes of a derby, brogue, loafer, or Chelsea boot. Recently though, we’ve clocked the people always one step ahead of the wave sporting an all-together more elevated leather boot. You may have seen our recent post on how men want to wear purses, they just don’t know it yet. Could the same be true of heels?

In the recent seasons whereby “Western” emerged as a big trend on runways, the Cuban heel has been a mainstay of labels such as Calvin Klein and Saint Laurent. On top of this, the style has been a go-to for some of the most prolific well-dressed male celebrities, with Harry Styles and Luka Sabbat following in the footsteps of Mick Jagger and Prince before them. Now, more than ever, flat-footedness seems to be the less fashion-forward option.

Some of the most well-thought-of luxury sneakers now tend to add an extra inch, Cuban heels are being adopted by more and more labels, and then there’s the new wave of ankle boots, with height not far off a woman’s high heel. Leading the trend is Maison Margiela, whose heeled Tabi boots have been making their debut around Highsnobiety HQ in recent times. Along with its stand-out height, Margiela’s Tabi doubles down on fashion points with its signature split toe-box, modeled after the Japanese style socks and footwear dating back as far as the 15th century.

Highsnobiety / Noah Thomas
Highsnobiety / Noah Thomas

Granted, trading in your sneaker rotation for this emerging trend is no small step. Here’s what Highsnobiety sneakerhead Noah Thomas has to say about the boots:

“For those who might be new to a heel, it will definitely take some getting used to,” says Noah. “But you may not be aware that men actually wore heels first, so walking in them is a lost skill we should relearn, especially now that they’re making their fashion comeback.

“Making the Tabi your first introduction into the world of elevated soles is a dive headfirst in the deep end, but it’ll make every other boot after that a walk in the park. The minute you put them on, you notice the slit. I’d recommend getting tabi socks because wearing them with normal ones creates a rather uncomfortable bunch up at the divide. You can get them in bulk on sites like Amazon for a very reasonable price if you don’t want to buy the Maison Margiela ones.”

Other fashion house iterations of this particularly high boot include Random Identities‘ Vibram sole version and Gucci’s altogether more rock’n’roll offering, which has emerge at some of our favorite luxury retailers done out in all-over GG Supreme logo print and vibrant red patent leather. For those who aren’t quite ready to strut so boldly, however, under the direction of Raf Simons, Calvin Klein 205W39NYC’s harness and Chelsea boots are some of the label’s greatest yet.

Browse more of our picks below, and let us know if you’ll be trading in your kicks for a higher heel any time soon in the comments.

Worker Boots

Random Identities


Painted Tabi Boots

Maison Margiela


Tabi Boots

Maison Margiela


GG Logo Boots






Chelsea Boots

Saint Laurent


Western Chris Crosta Chelsea Boots

Calvin Klein 205W39NYC


Tex Harness Boots

Calvin Klein 205W39NYC


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