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.
Minimalist yet striking—these slingbacks go with absolutely everything.
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.
Aquazzura
Passions Pumps 105
Sleek, sharp, and seriously glamorous—shoes made for turning heads.
MANOLO BLAHNIK
Bb 70 Canvas Pumps
Understated luxury at its best.
GIANVITO ROSSI
Amelia 85 Patent-Leather Pumps
TOM FORD
Angelina Croc-Effect Leather Point-Toe Pumps
Power dressing in a shoe.
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.