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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Pump the Brakes on Booties—Kate Hudson Knows the Better Fall Shoe Trend to Pair With DressesThis outfit combo is top-tier.
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Fall Is Almost Here: These Are the Classic Shoes I'm Most Excited to WearFrom ballet flats to Mary Janes.
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I Just Found Fall 2025's Biggest Shoe Trends All atReplica StoreNew season, new shoes.
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It's Happening, People: These It Loafers From 1953 Are Back From the DeadReady or not.
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Black Sandals Are Nice and All, But in NYC, Everyone Knows This Shoe Color Looks Chicer With White PantsThe unexpected choice is always a winner in this particular city.
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Don't Wear Leggings to the Airport Without Seeing Lindsay Lohan's Much Chicer AlternativeYes, it's still comfy!
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This Is the "Dated" Heel Trend to Buy Instead of Basic Pumps If You Want Cooler Outfits This FallSophie Turner is making the switch.
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French Women Have Decided These 3 Shoe Trends Are Officially Chicer Than Flat SandalsI'm following suit.
