Flats might feel better on your feet, but let's face it—no shoes make an outfit look chicer and more elegant than a pair of classic stilettos. Whether you opt for a kitten-heel version or go full Zendaya with a 100-millimeter heel, it doesn't much matter as long as the lifting option you choose is as skinny as a pencil and the toe at the other end is pointed.
I, for one, can't wait for people to get their act together, and by that I mean put their flats into storage and bring back fashion's most timeless shoes. Fortunately, I don't think I'll have to wait long. For starters, I just returned from Milan Fashion Week, where classic stilettos were the shoes of choice for showgoers and locals alike. At the Gianvito Rossi presentation for fall/winter 2025, the Italian designer displayed his signature pumps in over 30 shades of suede, leaning into the tried-and-true silhouette for the season ahead. Trendsetting ready-to-wear brands like Prada and Saint Laurent are, too, opting for simple and refined skinny-heeled pumps in supple satin (Prada) and patent leather (YSL).
Another reason for this style's comeback? Angelina Jolie, of course.
On Angelina Jolie: Dior bag; Manolo Blahnik BB 90mm Suede Pumps ($825)
The Maria actress was spotted outside of Atelier Jolie—her New York City atelier (featuring a boutique, customization workshop, and café) located on Great Jones Street in the former home of artist Jean-Michel Basquiat—wearing a very Angelina Jolie ensemble: a black suit with a white scoop-neck top underneath, paired with a Dior St. Honoré bag and Manolo Blahnik suede pumps. She's Wholesale Replica Bag in a slew of stiletto sightings this year, and she won't be the last. Scroll down to shop the chicest and most anti-trend shoes, well, ever.
Shop stilettos:
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Not Linen, Not Denim: The Far Chicer Pant Trend Fashion People in Turkey Are Wearing With White Tank TopsFashion icon Rosie Huntington-Whiteley approves.
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This Is the Classic Black Shoe Tasteful Dressers Wear With Jeans and a White Tee to Make Them Look ChicAs seen on Molly Gordon.
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The '90s Dress-and-Shoe Pairing It Girls Are Wearing to Parties in East Hampton (Sorry, Flip-Flops, You Weren't Invited)Classic elegance spotted at Gucci's star-studded soirée on Long Island.
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This Is, By Far, the Sexiest Shoe Trend to Wear With Jeans Right NowSee and shop the style inside.
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Just to Be Clear, *These* Are the Pants Fashion People in L.A. Are Wearing Instead of Basic JeansSpotted in Paris too.
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Owning Any of These 7 Summer Shoe Trends Is a Sign of Good TasteIYKYK.
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L.A. It Girls Are Swapping XL Totes for the Elevated Bag Trend Made for Pilates and Matcha RunsHailey Bieber being one.
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Fashion People in NYC Just Found a New Shoe Color Trend That Makes "Basic" Minidresses Feel So FreshHint: It's not butter yellow.
