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 the latest 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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The Expensive-Looking Sandal Color Every Fashion Person Is Wearing With Shorts and Dresses (Hint: It's Not Navy)It's not brown either.
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The Classic Swimwear Trend L.A. Fashion People Are Swapping Their Bandeau Bikinis ForNo fuss.
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This Casual Red Carpet Jewelry Trend Is Seconds Away From Being EverywhereMaximalism is so back.
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Red Who? Sorry, But Cool Fashion People Are Only Interested in Wearing Jeans With *This* Sneaker ColorIt's the new red (and yellow, green, and silver).
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It's Not "Ugg Season," But Cool Fashion Girls Know the One Outfit That Makes Them Year-Round ShoesFollow Bella Hadid's lead.
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Put Down the Sneakers—*These* Are the Flats Everyone Everywhere Will Be Wearing With Dresses This SummerTrust us.
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I Found It: The Only Denim Trend That Makes Flip-Flops Look Sophisticated Instead of CheapIn Kendall Jenner we trust.
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If I See You Swap Your Classic Ballet Flats for This Specific Alternative, I'll Know You Have Chic TasteDon't think about it—just do it.
