How the Dorky Men’s Square Toe Became the ‘It’ Style for Women This Fall

“Are Square-Toe Shoes the Nickelback of Men’s Fashion?” reads one headline from dating back to May 2017. In a post-Met Gala analysis of male red carpet looks, the writer debates the pros and cons of the shoe shape, pointing to Jaden Smith and ASAP Rocky as two guys who maybe, kinda, sort of pulled off the look, though the article ultimately concludes with an ambiguous warning. A video from the same year even went so far as to spoof a PSA, aligning “square-toe shoe syndrome” to something as shameful as a venereal disease. “1 in 7 men suffer from S.T.S. on a daily basis” reads its caption.

A pariah in the canon of esteemed men’s dressing, the square toe has long been a glaring DON’T. So how did it come to be one of the biggest new shoe trends for women?

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Caroline Daur during Paris Couture Week in July wearing an Acne Studios dress and square-toe pumps from the brand’s fall ’19 collection.
CREDIT: Shutterstock

Fashion’s ongoing obsession with the ‘90’s offers a big clue. Emerging brand By Far’s entire collection of shoes and handbags is practically built on styles from the minimalist decade. Sling backs, mules and strappy sandals feature kitten heels and, yes, square toes — all styles that until very recently were considered démodé —”mom shoes” before “mom” or “dad” anything was considered cool. “We source our greatest inspiration from TV shows and movies,” Sabina Gyosheva, one of By Far’s founders, recently told FN. “You often find us binge-watching ‘Friends’ and ‘Sex and the City,’ obsessing over their cool outfits.”

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By Far’s Diana sling back with a tapered square toe, inspired by the heels worn by Princess Diana in the ’90’s.
CREDIT: Courtesy of Moda Operandi

For fall, the brand is debuting the Diana, a sling back done in baby-blue, croc-effect leather, with a crystal embellished kitten heel and the hint of a square toe. But the simple two-strap slide on the Tanya sandal, with a slanted square toe and geometric block heel, has already dominated this summer. And By Far’s best-selling handbag is also something of a square: Its Rachel bag (named, of course, after Jennifer Aniston’s “Friends” character) has the sort of rounded shape that might elicit a cringe from the older millennials who carried it in high school. But it’s also the everyday bag carried consistently — without paid partnership — by Bella Hadid and Kendall Jenner.

By Far’s Tanya leather mule, one of the trend’s inaugural styles.
CREDIT: Courtesy of Net-a-Porter

Other brands have done well purveying the square toe as something that’s hip: Staud’s Gita sandal also comes with a slanted square toe and a curved kitten heel that reads as ’90’s mom. Co-founder and creative director Sarah Staudinger gets much of her inspiration from her own mother, herself a designer in the ’80’s and ’90’s who had her own shoe label. “My falling in love with fashion was during the ’90’s, when I saw [my mom] walking around in her kitten heels,” Staudinger recently told FN.

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Staud’s Gita sandal with a slanted square toe on the sole.
CREDIT: Courtesy of Net-a-Porter

But fashion’s biggest obsession with the quirky new shape lies with Bottega Veneta. Ever since its new creative director, Daniel Lee, sent out puffy quilted pumps with exaggerated, so-ugly-they-must-be-cool square toes as part of his debut collection for fall ’19, insiders have gone gaga for the brand. It’s even being called the “new-old Céline,” filling the void of thoughtful, sophisticated but still slightly quirky ready-to-wear and accessories left by Phoebe Philo when she exited Céline in 2017.

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Bottega Veneta fall ’19.
CREDIT: Shutterstock
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Bottega Veneta quilted puffy leather pumps.
CREDIT: Courtesy of Bergdorf Goodman

There’s no denying the Philo halo of Bottega’s new look, especially when it comes to the footwear. The designer was putting forth plenty of square toed “ugly shoes” during her Céline heyday, styles that designers are still referencing and street style stars are still wearing.

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Vogue Ukraine fashion director Julie Pelipas at Paris Couture Fashion Week in July wearing a pair of mismatched, square-toed sandals from Céline’s spring ’17 collection.
CREDIT: Shutterstock
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Bottega Veneta’s mesh square-toe shoes on the street during Paris Couture Week in July.
CREDIT: Shutterstock

For its new resort ’20 collection, Bottega continued on the square track, with cutout sandals, mesh thongs and a continuation of its braided slide sandals, styles that could very well become the 2020 version of Gucci’s must-have Princetown mules.

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Bottega Veneta’s metallic square-toe cutout sandals for resort ’20.
CREDIT: Courtesy of Bottega Veneta
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Bottega Veneta resort ’20.
CREDIT: Courtesy of Bottega Veneta
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Square-toe thong sandals in Bottega Veneta’s new resort ’20 collection.
CREDIT: Courtesy of Bottega Veneta

Among the must-have women’s styles, Bottega even included a few pairs of square toes for men. Could this be menswear’s final frontier?

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Puffy square toe men’s dress shoes, part of Bottega Veneta’s resort ’20 collection.
CREDIT: Courtesy of Bottega Veneta

Watch FN’s video with Tory Burch and Tabitha Simmons below. 

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