heeled boots for men main Gucci Ion Rick Owens

One of the defining style stories of the 2010s was how sneakers, tracksuits, and sportswear subsumed fashion runways — and subsequently — the mainstream.

As luxury consumers began to favor comfort and ease, elevated athleisure like Gucci tracksuits and Balenciaga runners soon became go-tos for the fashion week set. However, the needle is shifting again and athleisure is making way for a slicker, dressier aesthetic that has shot brands such as Bottega Veneta and Jacquemus to the top of the fashion pyramid. Heels are back, too.

Interestingly, men have more options than ever when it comes to heeled boots. Naturally, the popularity of Maison Margiela’s Tabi boot certainly helped lower the guards of guys who felt anxious about wearing shoes with a noticeable rise, while style icons like Timothée Chalamet, Jaden Smith, and Luka Sabbat have also helped normalize the idea of wearing elevated footwear.

The Tabi’s return has burst the dam, and now men have a ton of heeled options to choose from. Find some of our favorites below.

Sucker for Gucci

Ebal Boots

from $1133


(Available at 5 Merchants)
(Available at 5 Merchants)

Gucci’s black leather heeled boots from SS18 have gold-toned hardware, a feline head embossed on the sole, and the word “SUCKER” printed on the back.

The salacious print comes from an unusual reference point: Andrew Cavendish, the 11th duke of Devonshire, who made amusing and ironic statement sweaters for his scandalous dinner guests at his stately home. (It could also be a euphemistic reference, too.)

Either way, it’s the kind of obscure and romantic cultural touchpoint you would expect from Alessandro Michele, who also made the boot available in pink and red.

Smooth and Shiny Cuban Heels

Cuban Heel Leather Boots


Our Legacy

Buy at Matchesfashion

Steadfast Highsnobiety office favorite Our Legacy has delivered an impossibly smooth Cuban heel that could be easily worked into most outfits for a dash of fine Swedish craftsmanship.

Constructed from an aniline-dyed leather to help retains the hide’s natural shine, the boots come with elasticated side panels, a Vibram Westerner outsole, and an incredible two-inch heel.

Chunky Eytys

Nikita Boots

Nikita Boots

from $300


(Available at 2 Merchants)
(Available at 2 Merchants)

The Nikita boots from Eytys are for those who want to add a grunge option to their winter footwear rotation. Pair them with a leather trench and some small sunglasses and you’re basically in the Matrix.

Crafted from polished full-grain leather, the chunky rubber soles are offset with a shiny plate on the cap of the toe and the label’s signature purple on the pull tabs.

The Statement Color

Number 5 Boots





Buy at ln-cc

ION comes from Finnish-born shoemaker Achilles Ion Gabriel, who launched his namesake footwear and clothing label earlier this year. The red Number 5 Boots feature a soft leather finish, a squared-off toe, a hand-painted rubber-coated wooden sole, and silver-tone metal hardware on the zips.

Glam-Rock Shock

KISS Boots

KISS Boots

from $1103

Rick Owens

(Available at 4 Merchants)
(Available at 4 Merchants)

Rick Owens recently released his FW19 “LEGASPI” collection, which tied in with one of his new books that released last month. Owens says his obsession with pioneering costume designer Larry Legaspi stems from the fact “he introduced a camp ferocity to the mainstream and helped set a lot of kids like me free with his art deco sexual ambiguity.”

Channeling said camp ferocity, Owens’ most compelling footwear from this season comes in the form of a platform high-heeled boot, which adds about three inches. They’ve been worn on the runway, regularly by Owens himself, and recently out and about by his muse-slash-model-slash-collaborator Tyrone Susman.

  • Product Curator: Rhianna Matthews
Words by Max Grobe
Associate Fashion Editor