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:
-
The Pretty Flats Trend Katie Holmes Just Wore Makes Any Jeans Look High-EndFound my next purchase.
-
This Elegant Skirt Trend Resurfacing Just in Time for Spring Was Destined to HappenFollow Zoë Kravitz's lead.
-
These Are the 7 Stylish Shoe Trends Fashion People Will Be Wearing With Jeans This SpringI see chic denim outfits in your future.
-
Zara Just Delivered 8 Spring Shoe Trends That Will Make Your Outfits Look 10 Times ChicerFrom chic T-bar silhouettes to cherry-red shoes.
-
2025's Next It Sneakers Just Landed in Paris, so It's Only Days Before They'll Completely Sell OutRun.
-
30 Chic Spring Pieces I'd Love to See Jennifer Lawrence, J.Lo, and Katie Holmes Wearing Right NowI want every last piece.
-
I've Lost Count of the Number of Celebrities I've Seen Carry This Genius Handbag TrendOr should I say anti-trend bag?
-
Meet Lexie Hull, TikTok's Favorite Shooting Guard Turned InfluencerI spoke with Athleta's newest Power of She Collective member.
