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.
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:
Sharp, sleek, and effortlessly polished—these Manolos are power dressing at its finest.
A sculptural heel with a high-street price tag? Consider us obsessed.
Minimalist yet striking—these slingbacks go with absolutely everything.
Patent shine meets all-day comfort—Parisian polish in pump form.
Sheer genius! Delicate tulle and leather trim for the perfect romantic touch.
Ballerina vibes, but make them runway. Ethereal elegance at its best.
Sleek, sharp, and seriously glamorous—shoes made for turning heads.
Understated luxury at its best.
I love.
Power dressing in a shoe.
The heel that does all the talking—no accessories needed.
An icon for a reason—flawless curves, a perfect point, and that red sole.
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Of Course, Alexa Chung Was the First to Step Out in Miu Miu’s Next It FlatsThe perfect debut.
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Hold The Jeans—These “Dated” Trousers Make Your Boots, Loafers and Flats Look Extra Chic This WinterHoly smokes.
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I’m Not Bothering With Stilettos—This is the Chic Flat Shoe Alt Sarah Jessica Parker and French Women are Wearing InsteadA worthy alternative.
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New York It Girls Agree—This is the Coolest Heels Trend to Pair With Skirts Right NowI have to say, I agree.
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Not Wedges, Not Stilettos—This Is the New-Season Heels Trend Fashion People Are Wearing InsteadThe chicest upgrade.
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First VB, Then Kate Middleton, Now Alexa’s Also Choosing This New Shoe TrendLoved by a princess, a former pop star and an It girl.
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Spotted on the Red Carpet in London: The Affordable Basic You Can Buy at M&S, Zara and H&MWhen high street becomes high fashion.
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Sorry, Stilettos, Every Fashion Person I Know Is Elevating Their Winter Looks With This Heel TrendIt's my one recommendation.
