On Point

The pointed-toe shoe is a fashion staple that has returned in style decade after decade in slightly different variations. Whether you prefer pairing pointy flats with casual streetwear or pointy stilettos and slingbacks for special occasions, they give an effortlessly chic element to any look. This year, they have made another comeback with pointy pumps and slingbacks marking many prominent celebrity looks the past summer and staying with us into the colder season. But where does this iconic piece of footwear come from, and how did it stay relevant for so long?

Kendall Jenner wearing Bottega Veneta’s spiky slingbacks with a David Koma dress. Via IG @danixmichelle. Retrieved via British Vogue. © All rights belong to their respective owners. No copyright infringement intended.

Pointed-toe shoes have an unexpectedly rich history that, believe it or not, dates back all the way to the Middle Ages. In the medieval period, these shoes were exclusively flats and were worn as a symbol of wealth and high status. They were worn by both men and women, often of noble or royal descent. The shoes had flat soles but exaggeratedly long and pointed toes. They were especially famous in medieval London, where they even had a controversial history of being frowned upon by the church since they were seen as a symbol of sexual deviance. Pope Urban V even banned them for a period of time, but that didn’t seem to stop anyone from wearing them, so they persisted as a trend even through this period.

However, the design started evolving and becoming more refined, with time also being much more associated with femininity and women’s fashion. Their first prominent rise in popularity in the 20th century was in the 1920s, during the flapper era which saw a revival of pointed-toe shoes combined with lower, more practical heels. During the 1950s and 1960s, stiletto heels started rising in popularity, and they perfectly complemented the pointed-toe design. Pointed-toe heels very quickly became a symbol of femininity, grace, and confidence, and big Hollywood stars such as Marilyn Monroe and Audrey Hepburn took to wearing them, which made their popularity even more global. One of the designers who contributed to the innovative pointed-toe heel designs was Roger Vivier for Dior, who wanted to achieve the illusion of elongating the leg while also making stilettos synonymous with high femininity and glamour.

During the 1970s, they took a backseat as the world of fashion leaned more into natural and bohemian aesthetics, and less restrictive, more relaxing styles took center stage. However, a decade later they were back in full swing. The 1980s brought a focus to power dressing, bringing sharp and tailored looks that went well with pointed-toe heels and stilettos. The '80s brought bold colors and metallic finishes to the designs, and brands like Manolo Blahnik became popular in the fashion circles. Manolo Blahnik was especially known for stilettos that exuded glamour and luxury, which made them so high in demand and a real style and status symbol.

Minimalism in fashion was brought back in the 1990s, and it definitely dominated the footwear style of the decade. Pointed-toe shoes in sleek and neutral tones were the most popular design, and there was a high demand for variations of pointed-toe ballerina flats, as well as kitten heels. Even though the grunge movement was also very prominent in the '90s, high fashion retained predominantly sharp and sleek looks. The new century continued with similarly designed pointed-toe kitten heels, ballet flats, and stilettos, but some high fashion brands stepped into more popularity and popularized them even further, such as Jimmy Choo and Christian Louboutin. They focused on luxury branding but also creative, daring designs. However, the end of the decade saw a rise in round-toe and almond-shaped shoes, which posed competition to the pointed-toe styles.

Contrary to power dressing and wearing stilettos as a symbol of powerful femininity and dominance, in the 2010s it was more about versatile designs, and combining elegance with comfort. Trends that emerged around sustainability in fashion also inspired the usage of more practical materials and timeless designs. One of the brands that introduced new pointed-toe designs in the 2010s was Celine.

In the current decade, pointed-toe shoes, both in the form of heels and flats, remained a must-have staple. However, they kept evolving and assuming bold new forms, combining mixed materials more and more. With Jimmy Choo, Christian Louboutin, Manolo Blahnik, and Bottega Veneta being at the top when it comes to pointed-toe heels, fast-fashion brands have also taken this style on and made lesser-quality but more affordable versions. Pointed-toe shoes still continue to captivate fashion enthusiasts, and this year that was reflected in the number of iconic celebrity looks that incorporated them, like Beyoncé’s custom Jimmy Choo heels worn as a part of one of her Renaissance tour outfits. With new styles, materials, and heights being constantly created, pointed-toe shoes are sure to stay a fashion staple in future decades as well.

Sonja Stojiljkovic

Born and raised in Serbia, Sonja has always dreamed of living in different places and absorbing different cultures, which brought her to study in the Netherlands. She has recently graduated with a degree in Communication and Media. Sonja has been a passionate reader, writer, and art lover ever since her childhood days. A melancholic and romantic who loves nothing more than soaking up experiences, most of her money goes towards concerts and trips where she aimlessly walks through museums and enjoys local food. 

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