It’s a Witch! It’s a Pilgrim! It’s a Y2K Raver! Why Square-Toe Shoes Are Back in Style

That magic has apparently been rekindled. Digital trend tracker SEM Rush saw a 2,500% increase in web searches for “women’s square-toe shoes” between July 2021 and July 2022. Meanwhile, online shopping platform Lyst offers over 24,500 women’s square-toe shoes, including faux leather updates from Ms. Cleveland’s Courrèges pair and other Judy Jetson-esque riffs from Dries Van Noten and Rupert Sanderson. The sharp-edged silhouette can convey more than cosmic style: Prada’s slingbacks evoke the stealthy wealth of ’90s celebrities, while Versace’s satin slides evoke the Y2K candy rave scene. The trend also points to the ballet’s pointe shoes, which inspired recent versions of Sandy Liang, Mansur Gavriel and Khaite. Meanwhile, actress Selma Blair says her Salvatore Ferragamo square-toe loafers are “the granny shoes I love Love.(She’s currently wearing them with tied khakis in her new Gap campaign.)

The history of the form is complicated. According to Sarah Collins, professor of fashion at the Savannah College of Art and Design, the square was first popularized in the West by Henry VIII, who ruled England in the 16th century. A century later it crossed the Atlantic on the feet of male pilgrims, whose plain black versions signaled the spiritual value of Puritan austerity. It wasn’t until the 19th century that square toes became synonymous with feminine beauty, when ballet master Charles-Louis Didelot championed box-toe pointe shoes that allowed dancers to levitate onstage. Captivating to behold and excruciating to wear, they remain symbols of bloodstained discipline to this day.

In the 1940s, shoes took on a sturdy steel-toe form as women entered the workforce during World War II. Square-toes reappeared in the ’60s, Ms. Collins said, when “women rebelled against ’50s domesticity” and wore shoes with hard edges and low heels for better mobility. Around the same time, shoes began to mimic the angular “feet” of metal robots, making the wearer appear more machine than human. The blunt shape “turns part of the body into architecture,” said Olivier Leone, the co-founder of Parisian footwear brand Nodaleto, whose square-toe heels often sell out at Net-a-Porter. “Therein lies beauty and power.”

To channel that power yourself, Lisa Virtue, vice president of women’s design at label 7 for All Mankind, suggests following the trend by pairing the shoes with wide-leg jeans: “It’s my favorite way to wear them [a square toe] because it just pops.” For those with bolder fashion goals, Hollywood costume designer and stylist Zerina Akers recommends choosing vibrant, patterned shoes that don’t evade attention. The Emmy-winning fashion insider has beveled Beyoncé’s appendage and often wears the shape herself. She thinks it’s comfortable, unrestricted, and pretty cool. “Busy women need to move,” she said. “The wide shape makes it easier and still looks chic.” Johanna Alter Wilson, 53, owner of Strategic Financial Group, Inc. in Englewood Cliffs, NJ, likes good-looking, human, square-toed toes in the office and at lunch with friends . “Pointed shoes are not common among older women. They kill everyone I know who is over 50,” she said, adding that square toes are “very European.”

However, the trend can be polarizing. When I showed the coveted Bottega Veneta Tower platforms to a private equity friend, she winced and said the square toe shape “makes you look like a Lego person or a Metaverse sex doll.” As I walked down Manhattan’s Upper West Side, a little girl stared at my Everlane square-edged ballet flats and yelled, “Daddy! Your shoes are creepy!” Perhaps she had read Roald Dahl’s novel The Witches, which suggests that sorceresses “have no toes. They only have square-ended feet.”

For women who make their own magic through style, Dahl’s claim is spot on.

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