We Charted Exactly How Square-Toe Shoes Became Chic Again

By Far
A woman sitting next to a pool in square-toe heel sandals

For The Zoe Report’s Trace The Trend series, we investigate the real story behind how your favorite trends got their starts. Here, a look at the history of square-toed shoes — and how they became one of 2019's most iconic looks.

There are shoes that you wear for a season or two, and then there are shoes you identify with. If you've embraced 2019's square-toed shoe trend, the style is undoubtedly the latter for you. There's something about a square-toed shoe that feels a little more brazen and showy, corners sharpening where roundness once prevailed. It's also surprisingly controversial, its upticks and falls in popularity feverishly tracked by fashion writers. (In a 2017 article titled "The Square-Toe Shoe Must Die," GQ called the silhouette a "geometric disgrace.")

And this may make the shoe all the more attractive. “I think they are visually dissonant — at least the more extreme versions seen in current collections,” Dr. Rebecca Arnold, senior lecturer in history of dress and textiles at the Courtauld Institute of Art, tells The Zoe Report over email. “For some people a curved toe completes the overall silhouette smoothly, while the square toe seems blunt and incomplete. I think it’s a matter of what we are used to visually — and whether we feel comfortable to break with that or not.”

Our design is very much influenced by iconic TV shows from the '90s such as Friends and Sex and the City.

These days, all it takes is a scroll through Instagram to see the square-toed shoe in action. Its appearance in the catalogs of designers and on the feet of industry insiders has solidified it as a defining look of 2019. But for many, the square-toed shoe also holds nostalgic appeal; its resurgence heralds back to the '90s when the style was seen everywhere from the runways to pop culture — and indeed, some designers admit that's exactly where they get their inspiration. "Our design is very much influenced by iconic TV shows from the '90s such as Friends and Sex and the City," says Valentina Ignatova, a founder of the Insta-famous (and often square-toed) shoe brand By Far. "We’re also constantly sourcing inspiration from the aesthetics of Prada and Calvin Klein from the '90s."

Courtesy of By Far

However, to view square-toed shoes strictly as a ‘90s comeback is to ignore the cyclical nature of fashion — and the history of the style. So, what came before the ‘90s trend we all know and (most likely) love? Well, quite a bit, actually.

300 B.C.–300 A.D.

Universal History Archive/UIG/Shutterstock

While a square-shaped shoe style has appeared in cultures all over the world, one of the earliest examples of square-toed shoes is the Japanese geta and zōri. Although, as Rie Nii, a curator at the Kyoto Costume Institute and promotional staff on the exhibit "Dress Code: Are You Playing Fashion," tells TZR over email, it may be impossible to attach an origin date to the traditional sandal-like footwear. "I have never seen the exact year in any books... it’s ancient," Nii says of the stilted, square geta. "Lots of 'ta-geta' (used to protect feet and prevent sinking in paddy fields and wetlands) have been found from archaeological sites in Japan," Nii adds, pointing to a relic found in the Shizuoka prefecture that dates back to the middle to late Yayoi era — around 300 A.D.


The square-toed style appeared just as nebulously in Europe, though many, many years later. "I think currently it is very difficult to pinpoint the first example or examples of square-toe shoes," Rebecca Shawcross, senior shoe curator of the Northampton Museum and Art Gallery, tells TZR over email. "Illustrations and references from earlier than 1610 largely show shoes with points of varying degrees, the most exaggerated being the medieval poulaine — or more foot-shaped toes and round toes." (A poulaine is the extremely long, pointed-toed shoe that often comes to mind when you think of medieval footwear.)

"By 1500, the pointed-toe poulaine went out of favor to be replaced by the very wide-toe shoe known as a footbag, as it was like putting your foot into a bag," Shawcross says. "The complete opposite of the poulaine in terms of shape, the footbag was flat-soled but had a broad toe. Most of the time these shoes had rounded toes but the shoes followed the horizontal lines evident in the square, boxed, padded shoulders and wide shoes that were typified by the English King, Henry VIII."

An 1877 illustration of "shoe fashion from the Middle Ages." imageBROKER/Shutterstock

And, speaking of the king, Shawcross also looks to a 1537 painting of the monarch by Hans Holbein for evidence of him wearing the square-toed style. "I’m sure the portrait of him from Liverpool’s Walker Art Gallery shows him in wide square toes," Shawcross says. "Hammer-head toes that resembled the end of a hammer could be said to be square, too."


Square-toed shoes managed to find their footing at the beginning of the 17th century amongst the non-royals — aka most people in Europe. "Styles were being introduced and then filtering down through society from top to bottom, but also out from towns and cities where the style first appeared. It could be quite a slow process," Shawcross says. "By 1610-20, toes became square after a period of pointed toes. I think they were considered practical and quite sensible."

Wikimedia Commons/Public Domain / By Daniël Mijtens

The practicality of the simple shape seemed to parallel that of the Japanese geta in some ways. Shawcross points to an early 1630s oil painting of Henry Rich, 1st Earl of Holland, from the National Portrait Gallery of London. "[It] shows him wearing square-toed shoes with the extended sole under the heel creating a flat-soled galosh so the shoe wouldn’t sink so much into soft ground," Shawcross says. "Though of course, how successful this was is open to speculation."


1770s. Historia/Shutterstock

According to the BBC, the end of the 17th century also spelled the end for unisex footwear — with an article on heels in menswear by William Kremer pointing out that women's shoes began to be tapered to appear slender. "When talking about women and their feet/shoes, the ideal foot is small," Shawcross says. "This has always been the case, this included during the 18th century when women could create the illusion of having small feet by just showing the toe peeking out from the skirt. This was helped if the toe was pointed and not square."

That's not to say square-toed shoes for women were unheard of. Shawcross notes that while men often wore squared dome-toe shoes (similar in toe silhouette to modern combat boots), women sometimes wore square-toed mules and latchet tie shoes secured with a buckled strap — though these styles "are at the furthest end of what we would consider a square toe today," Shawcross says. Pointed toes in women's shoes can be spotted as early as the 1660s, creating a divide in "what are considered men’s styles and what are considered women’s styles," she adds.


1816. Historia/Shutterstock

Yet, somehow, the square-toed shoe found its way back to women in the 1800s. "From the turn of the 19th century, the heel on women’s footwear became lower and lower until it disappeared altogether," Shawcross says. "Toe shapes softened until the typical style for women by the 1840s was the simple, flat-soled, square-toe, slip-on shoe, with ribbon ties to help keep them on the foot. 'Flats' complemented the fashions of the day for large puffed sleeves, tiny pulled-in waists, and bell-shaped skirts. As skirts increased in width, so they became shorter, drawing all eyes to the foot, typically shod in jewel-colored silk and satin slip-on shoes or ankle boots."

Such shoes confined women again to the indoors. These shoes would have seriously suffered being worn outside and are totally impractical.

Nevertheless, this did not harken a return to genderless footwear. "Although it sounds like a step towards masculine square toes again, the shoes that sported the square toe were anything but masculine. They were similar to the ballet shoe — delicate, dainty, and flimsy," Shawcross says. (Interestingly, the style's popularity mirrors the rise of pointework and ballet itself in the 19th century.) "They were not outdoor shoes, as they were largely worn indoors or when attending balls. Such shoes confined women again to the indoors. These shoes would have seriously suffered being worn outside and are totally impractical. So they may have the square toe, but everything else about them screamed delicacy and femininity."

Early 1900s

1943. Historia/Shutterstock
1936. Historia/Shutterstock

History-minded fashionistas may be able to note a correlation between the shoe's popularity in the early 20th century and the rise (and subsequent fall) of war-inspired utilitarianism. "Square-toed shoes were fashionable in the 1930s, especially from the middle of the decade — they are quite subtle and elegant, as the fashions were more streamlined at the time," Arnold says. “Some of the square-toed shoes are sturdier designs for walking in the city, and refer back to pilgrim styles. This fashion continues into the ‘40s, and is revived, but is far less popular in the following decade, when rounded or pointed silhouettes dominate."

"You do see a lot of square toes in the 1960s though,” Arnold says. “Again, it is just the very end of the shoe that is squared off — so as in previous decades, the overall look remains narrow."


July 2, 1961. Underwood Archives/UIG/Shutterstock

Shawcross notes that the early ‘60s brought on a "modified court shoe design" — otherwise known as pumps — from the British shoe brand H. & M. Rayne; she adds that the style was a reaction to pointed-toe stilettos, which were "starting to lose favor." "This new style had a blunt, square toe, often called the ‘chisel’, while the upper was widened and elongated to make it more spacious and comfortable to wear. It sported a reasonably high, but thick, heel," Shawcross says. "The design was a success and found favor on both sides of the Atlantic, especially with such influential types as the Duchess of Windsor and Jacqueline Kennedy."

Since the latter half of the ‘60s, a square toe came into trend. Céline, Dior, Yves Saint Laurent, Charles Jourdan… all famous houses made square toes.
Wikimedia Commons

"Since the latter half of the ‘60s, a square toe came into trend," Nii adds, pointing to a pair of blocky, mid-'60s Roger Vivier pumps famously worn with Yves Saint Laurents’ Mondrian dress, as well as Catherine Deneuve’s style in the 1967 cult-classic movie Belle de Jour. “Céline, Dior, Yves Saint Laurent, Charles Jourdan… all famous houses made square toes.”

Christian Dior shoes from the late '60s. Courtesy of Northampton Museum and Art Gallery

"An eye-catching characteristic of the design was the addition of a decorative feature to the vamp edge — from diamanté to a rhinestone buckle," Shawcross says. "In the United States, such shoes were dubbed 'Pilgrim pumps', after the buckled shoes worn by Puritan pilgrims in the 17th century."


"After that, pointy pumps with high heels became the trend, while body-conscious dresses came in the ‘80s," Nii says. When looking back at the decade, square styles from Japanese designers such as COMME des GARÇONS’ Rei Kawakubo — who toyed with broad, square-toed silhouettes — seem even more jarring. "I think Kawakubo resisted the feminine fashion trend," Nii says.

Grosescu Alberto Mihai/Shutterstock

In turn, the avant-garde designer had a hand in inspiring one of the most popular, regularly squared-off shoes in fashion: Martin Margiela’s Tabi, which appears to have made its debut during Margiela's inaugural 1988 runway show. Although it may seem obvious by its name that Margiela's Tabi boot was inspired by the traditional Japanese tabi sock historically worn with geta, Nii also notes that the Belgian designer “was deeply inspired by Japanese designers, especially Rei Kawakubo.” (However, Nii also says that, in her opinion, Kawakubo's original square-toed shoes were not influenced by the shape of geta.)

"Tabi are divided so they can be worn with the thonged geta — but Margiela turns the sock into the shoe itself, which creates another shape entirely, making the foot look similar to a hoof," Arnold adds. "I think [it’s a] part of greater experimentation with footwear design and references to non-western and historical styles to rethink contemporary shoe fashions."



Rethinking classic styles seems to be a trend of the '90s — perhaps even more so than the square-toed shoes designers used to accomplish it. "There are so many varied historical references in 1990s footwear,” Arnold says. "From Vivienne Westwood’s fusion of renaissance and 1970s references in her square-toed platforms, to much more conservative 1960s-inspired square-toed and square-heeled slingbacks by various designers and mass market brands."

I think as we get closer to today it is more than evident that there are no new styles.

Nonetheless, there may be a reason why the quiet strength of square-toed shoes has caught on again now, as it did in the '90s. Ignatova says the design feels dominant, extravagant, and empowering, though "in a subtle, classic way." "Ever since the launch of By Far we were obsessed with the square-toe shapes," she says. "It felt more natural to us than the round toe. I remember visiting the studio always squaring the shapes, but it never felt as a risky move. It was only after we launched them that we realized that we’ve created something unusual and forward thinking."

So, what's next? And how long will square-toed shoes dominate? As with anything in fashion, there's no set timeline on the trend; though you should probably hold onto any square-toed sandals you bought this summer. "I think as we get closer to today it is more than evident that there are no new styles. There are some basic shoe styles, shapes of toe, types of fastening, and heel types. Fashions are still constantly having to change, but these basic styles come round again and again with a tweak by the designer or brand," Shawcross says. "Today’s designers will look to the past and recreate styles in their own way, but echoing what has gone before."

Ahead, five pairs of square-toed shoes to shop.