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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Amal Clooney Just Brought Back the Shoe Trend That's Been Losing Relevance for YearsIs it due for a resurgence?
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These Are the Classy, Expensive-Looking Shoes Cool Girls in NYC Are Wearing With Shorts This SummerThey make your outfit look more expensive.
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Put a Hold on Your Black Leggings—This Fresh Color Trend Is the One You'll See Everywhere This SummerThe "just right" shade that feels fresh and elegant for 2025.
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Brace Yourself—This "Ugly" '90s Sandal Trend Jennifer Aniston Used to Wear Nonstop Is Officially BackIt's about time, if you ask me.
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Spotted in Venice: Kylie Jenner Just Wore Summer's Most Controversial Dress TrendWe approve.
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If You're Over Kitten Heels, This French-Girl Heel Trend Is What Stylish People Are Wearing InsteadSpotted on Charlize Theron.
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The Surprising Shoe Trend I Spotted Everywhere in European AirportsNow boarding: Open-toed sandals.
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PSA: This Unexpectedly Elegant Dress Color Trend Is the New Butter YellowTake a page out of Hailey Bieber's style book.
