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 Wholesale Replica Bag 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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They're Here: 5 Expensive-Looking Shoe Colours That Will Instantly Make You Look Elegant and Put-TogetherAnd they're perfect for autumn.
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I Saw Zoë Kravitz, Hailey Bieber and EmRata Swapping White Tees for This Top Trend, So I Did TooNothing plain about this.
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Loves of My Life: Nicole Melillo ShawA (driving) force to be reckoned with.
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Begone, Boring Accessories—This Is the Shoe Trend Fashion People Are Hooked On This MonthAdd some interest.
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Don't Let Ankle Boots Have All the Fun—Personally, I Find This Autumn Boot Trend Even ChicerA wardrobe-altering buy.
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Katie Holmes Just Styled a Midi Skirt and Flats in the Most London-Girl WaySimple but chic.
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I’ve Been Secretly Wearing Celine's New Luggage Bag For Weeks— It’s Bound to Be the Next It StyleIs it better than the original, though?
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Not Classic Ballet Flats, Not Loafers—Everyone With Cool Style Will Be Wearing These Shoes With Black Trousers This AutumnAs seen on Katie Holmes.
