Andrea Pompilio is the Man Betting You’ll Wear a Sneaker Heel

The first look at Onitsuka Tiger’s Fall 2026 show in Milan was a pleated miniskirt and matching blazer, rib-knit knee socks, and a Mexico 66 reworked as a pointy-toed kitten heel. 

The Mexico 66 is the most sacred flat-sole shoe in the game. Bruce Lee wore it. Uma Thurman ran through Kill Bill in it. Right now it’s on the feet of every fashion editor, ballet flat convert and Depop girl in London. And someone just put it on a slingback kitten heel, no matter if you think it’s genius or sacrilege. 

That somebody is Andrea Pompilio, who’s had his hands on this exact sneaker since 2013, when it started as a co-branded shoe with his own name stitched onto it, and who’s been running the whole show as creative director since 2017. 

Pompilio is Italian, from Pesaro, raised partly in his grandmother’s clothes shop. He did time at Alessandro Dell’Acqua, Prada, Calvin Klein and Saint Laurent before starting his own menswear line in 2010, winning Vogue Italia’s Who’s On Next in 2011, and debuting at Milan Fashion Week in a slot Giorgio Armani hosted at his own Armani Teatro. The Onitsuka Tiger relationship started because Pompilio wanted sneakers for his own label, and sneaker-making simply wasn’t prevalent in Italy at the time. He ended up going to Japan instead where he was introduced to Onitsuka Tiger’s global head, and by 2013 the two were making shoes together at Pitti Uomo.

Since then he’s helped create the AW20 campaign that put Willow Smith alone in the desert, surrounded by earth tones and stillness. There was the Tokyo show built as a tribute to founder Kihachiro Onitsuka, whose company started in 1949 making basketball shoes with suction-cup soles, bizarrely inspired by octopus tentacles, and which eventually became ASICS. And then last year, the real coup was a Versace collaboration on the Tai-Chi sneaker and a matching loafer, both hit with Medusa hardware, the only collection Dario Vitale ever got to design at the house before he stepped down that December.

They’re already on the right feet. Industry star Myha’la has been photographed in them, and so has Guillaume Diop, who in 2023 became the Paris Opera Ballet’s first Black danseur étoile in the company’s 354-year history. 

So back to that first look: a miniskirt, a blazer, knee socks, and a childhood sports shoe on a heel. Whatever you make of it, you won’t have to wonder much longer. The Mexico 66 Kitten Heel starts coming to shops this month.