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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Hailey Bieber Wore Vintage Tom Ford Gucci Sandals With the Summer Pant Trend I See Sticking Around Through FallAny pants that look this good shouldn't be packed up just because the season changes.
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Kylie Jenner Just Declared This "Dated" Denim Trend Is Still In—But Only Styled *This* WayTake note.
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Spotted in East Village: Zoë Kravitz Just Paired $30K+ Worth of Jewelry With Every Fashion Person's Favorite Anti-JeansSorry, denim—your turn is up.
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Julia Garner Just Wore This Anti-Athleisure Shoe Trend With Leggings in NYCI did not see this coming.
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Forget Lace-Up Boots: This Casual and Easy Boot Trend Is About to Be EverywhereMake this your first boot purchase for the season.
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Forget Mules—*These* Are the Classic Anti-Flats L.A. It Girls Wear for Dinner at Giorgio BaldiGood food, great footwear.
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FYI: Every Fashion Person Is Buying This Pretty Shoe Color Instead of Black Right NowCount us in.
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Goodbye, Linen Trousers—Starting Now, This Pretty Pant Trend Will Be on Fashion People EverywhereI guarantee it.
