3 Classic Shoe Trends That Will Never Go Out of Style

last updated 22 November 2022

Zendaya looks away from the camera wearing a white headband and a checkered coat.

Are you a classic dresser or a trend lover? We write plenty of stories catering to both ends of the spectrum, but this one's for those who gravitate toward timeless pieces. While doing photo research for my Cannes Film Festival retrospective, I came across an image of Audrey Hepburn in 1960 wearing a pair of flats that looked strikingly similar to the Loro Piana ones Zendaya wore recently. The 64-year gap made me think of shoe styles that have been able to transcend trends throughout the decades.

Another popular shoe trend that celebrities have been wearing for over 50 years is T-strap sandals. Jackie Kennedy famously wore hers while on vacation in Capri, and Meghan Markle is known to wear them frequently. Finally, to round out this story, I included an image of Grace Kelly wearing ballet flats in Palm Springs in 1954, proving that the style has some serious longevity. Scroll down to see the photos and shop the trio of timeless shoes.

Pointy-Toe Flats: Then and Now

Audrey Hepburn wears a short-sleeve dress and flats, pictured with two other people.

Zendaya wears a gray sweater with gray trousers and green flats.

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Loro Piana

Rebecca Calfskin Ballerina Flats

You can't go wrong with Zendaya's exact pair of flats.

Flattered

Bodil Leather Ballet Flats

Sleek and simple.

MANOLO BLAHNIK

Maysale Suede Point-Toe Flats

This baby pink is perfect for summer.

T-Strap Thong Sandals: Then and Now

Jackie Kennedy wears a white short dress and thong sandals.

Meghan Markle wears a printed dress with thong sandals.

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Reformation

Thea T-Strap Flat Sandals

Don't overlook Reformation's fantastic shoe selection.

ANCIENT GREEK SANDALS

Lito Leather Sandals

These sandals can be styled in a million different ways.

AQUAZZURA

Almost Bare Metallic Leather Sandals

Aquazzura never gets it wrong.

Ballet Flats: Then and Now

Grace Kelly wears a T-shirt and shorts with ballet flats in a black-and-white image.

Sofia Richie wears a black and white dress with red ballet flats.

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Sam Edelman

Meadow Ballet Flats

Hurry: These cute shoes are currently on sale.

Dolce Vita

Reyes Mary Janes

I'm simply obsessed.

Schutz

Arissa Flats

These are perfect for the office.

Erin got her start as a Who What Wear intern in 2011—back when the site only published a single story per day. (We have since increased that number twentyfold.) She graduated magna cum laude from USC and lives in Los Angeles. In college, she also interned at Refinery29, where she was promoted to editorial assistant and then assistant editor. After nearly three years at R29, she came back to WWW in 2015, where she is now the Associate Director of Fashion News. From the Oscars to the Met Gala, she leads the site's entire red carpet coverage strategy. She specializes in celebrity and fashion news but also enjoys writing travel features and runway reports. She frequently contributes to WWW's social accounts and has a sizable following on her personal TikTok.