
I’m eager for people to move away from flats and revive this classy shoe trend.
Flats may be more comfortable, but let’s be honest—nothing elevates an outfit quite like a pair of classic stilettos. Whether you prefer kitten heels or go for a full 100-millimeter style like Zendaya, what really matters is that the heels are as slender as a pencil and the toes are pointed. Personally, I eagerly anticipate when everyone gets together to stow away their flats and revive these timeless shoes. Thankfully, I believe that moment is near. I just returned from Milan Fashion Week, where classic stilettos were the footwear of choice for attendees and locals. During the Gianvito Rossi presentation for fall/winter 2025, the Italian designer showcased his iconic pumps in over 30 suede shades, embracing this enduring silhouette for the upcoming season. Trendsetting ready-to-wear brands such as Prada and Saint Laurent are also favoring sleek and elegant skinny-heeled pumps in luxurious satin (Prada) and patent leather (YSL).
And who’s partly responsible for this resurgence? None other than Angelina Jolie. The *Maria* actress was seen outside her New York City atelier, Atelier Jolie—located on Great Jones Street in the former studio of artist Jean-Michel Basquiat—dressed in a quintessentially Angelina Jolie outfit: a black suit with a white scoop-neck top, complemented by a Dior St. Honoré bag and Manolo Blahnik suede pumps. She’s just one in a series of stiletto sightings this year, and certainly won’t be the last. Scroll down to shop the most stylish and timeless heels that are, well, ever.
Shop stilettos:
- Manolo Blahnik BB Pointed Toe Pump
- Manolo Blahnik Maysale Buckle Pointed Toe Pump
- Saint Laurent Norma Pumps in Patent Leather in Black
- Sam Edelman Hazel Pointed Toe Pump
- GIANVITO ROSSI 70 Suede Pumps
- Nordstrom Lexxy Pointed Toe Pump
- CHRISTIAN LOUBOUTIN Iriza 85 Patent-Leather Pumps
- Jeffrey Campbell Risktaker Pointed Toe Pump
- LK Bennett Floret Pointed Toe Pump
- MANGO Asymmetrical Heeled Shoes
- MANOLO BLAHNIK Terka 70 Bow-Embellished Poplin-Trimmed Satin Pumps















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I’m eager for people to move away from flats and revive this classy shoe trend.
There's just no other style like it.