Look of the Week: Alexander Skarsgård Breaks Fashion Norms with Thigh-High Leather Boots

While the Cannes Film Festival red carpet often sparks debates about long trains and daring dresses, Swedish actor Alexander Skarsgård flipped the script in a bold, unexpected way. What if, back in 2005’s Mr. and Mrs. Smith, it was Brad Pitt—not Angelina Jolie—rocking thigh-high leather boots?

That’s exactly the vibe Skarsgård brought to La Croisette on Sunday. Attending the premiere of Wes Anderson’s The Phoenician Scheme, he stunned everyone with a jaw-dropping pair of thigh-high boots. Designed by Harry Lambert and straight from Saint Laurent’s Fall-Winter 2025 runway, these square-toe boots wrapped his entire legs, stopping just where boxer shorts would begin. The look? Half dominatrix, half fisherman’s waders—and completely unexpected.

Thigh-high boots have long been seen as the ultimate symbol of female sex appeal. Angelina Jolie famously wore them as the seductive assassin Jane Smith, pairing them with fishnets, suspenders, and a strapless PVC minidress. Julia Roberts’ Vivian in Pretty Woman and Jane Fonda’s Barbarella also sported iconic tall boots. Even Anne Hathaway’s character in The Devil Wears Prada reached style perfection only after slipping on knee-high leather boots—leading to one of cinema’s most memorable fashion moments.

But here’s a fun fact: thigh-high boots weren’t always a women’s thing. They actually date back to the 15th century when men wore them for practical reasons. A medieval skeleton found in London’s Thames in 2018, believed to be a fisherman or sailor, was wearing boots that reached his thighs. Later, in England’s Restoration period, King Charles I and his Cavaliers donned riding boots that could either stand tall or fold into cuffs—often with heels to show status.

It wasn’t until the 1960s that thigh-high boots became linked with femininity and sex appeal. In 1962, Cristóbal Balenciaga introduced a knee-high boot, and a year later, Roger Vivier pushed the design further for Yves Saint Laurent, crafting alligator leather boots that reached up to the thigh. Vogue praised this evolution, saying, “This year’s best-looking legs will be marching up and down and back again in boots.”

This trend fit perfectly into the post-war “Youthquake,” a time when hemlines got shorter and sexual attitudes shifted. In Mary Quant’s era of the miniskirt, tall boots framed bare legs like never before—making them an icon of female empowerment and style.

Today, while thigh-high boots are a staple in women’s fashion, men wearing them is still a fresh idea. But pioneers like Pedro Pascal, who wore the same Saint Laurent boots earlier this year, are changing that. Designers like Rick Owens, Martine Rose, Givenchy, Maison Margiela, and GmbH have all embraced the trend, creating bold over-the-knee styles for men.

As fashion becomes more daring and gender boundaries blur, thigh-high boots on men feel like the next natural step. Whether paired with ballet flats or Mary Janes, these boots are proving that style is about courage and creativity—no matter who wears them.