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:
-
Here They Are: The 6 Biggest Boot Trends of Fall 2025Exotic finishes! Sock boots! Western motifs!
-
Paris Hilton's World: Her Pink Motorola Razr, Favorite Y2K Looks, and What 11:11 Media Means to HerA glimpse into the life of this savvy entrepreneur.
-
After 2 Weeks in Italy, I'm Convinced I Need the Shoe Trend Every Chic Woman in Milan and Rome Was WearingForget ballet flats.
-
Sorry, White Skirts—Zoë Kravitz Just Wore the 2025 Alt That's About to Be All Over NYC This FallThe perfect choice if ballet flats will be your go-to shoes for the season.
-
This Classic Shoe Is Every Parisian's Secret to Making Jeans Look Elevated in FallAnd you probably already own it.
-
This Timeless Shoe Trend Makes Every Black-Dress Outfit Look So '90sIt's an instant elevator, no matter the dress style. Just ask Jennifer Aniston and Rosie Huntington-Whiteley.
-
Not Classic Ballet Flats, Not Loafers—Everyone With Cool Style Will Be Wearing These Shoes With Black Trousers in Fall 2025As seen on Katie Holmes.
-
The 5 Shoe Trends *Everyone* Should Own, According to New Stuart Weitzman Ambassador Emma ChamberlainRead our exclusive interview.
