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, when I was at Milan Fashion Week a few weeks ago, 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.
(Image credit: The Image Direct)
On Angelina Jolie: Dior bag; Manolo Blahnik BB 90mm Suede Pumps (£650)
The Maria actress was spotted outside of Atelier Jolie—her New York City atelier (featuring a boutique, customisation 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 Our Favourite Chic Stilettos:
MANOLO BLAHNIK
Bb 90 Leather Pumps
Sharp, sleek, and effortlessly polished—these Manolos are power dressing at its finest.
MANGO
Asymmetrical Heeled Shoes
A sculptural heel with a high-street price tag? Consider us obsessed.
Christian Louboutin
Miss Z Patent Leather Pumps 100
Patent shine meets all-day comfort—Parisian polish in pump form.
JIMMY CHOO
Lotta 45 Leather-Trimmed Tulle Pumps
Sheer genius! Delicate tulle and leather trim for the perfect romantic touch.
AQUAZZURA
65 Satin-Trimmed Ruched Tulle Point-Toe Pumps
Ballerina vibes, but make them runway. Ethereal elegance at its best.
Dolce & Gabbana
Patent Leather Logo Pumps 90
The heel that does all the talking—no accessories needed.
CHRISTIAN LOUBOUTIN
Sporty Kate 85 Leather Pumps
An icon for a reason—flawless curves, a perfect point, and that red sole.