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 choose a kitten-heel style or go for a full-on 100-millimeter heel, what matters is that the heel is slender as a pencil and the toe is pointed. Personally, I’m eager for people to embrace this trend again, which means putting away their flats and reinstating these timeless shoes. Thankfully, I suspect that won't take long. During my visit to Milan Fashion Week a few weeks back, I noticed that classic stilettos were the favored footwear among attendees and locals. At the Gianvito Rossi fall/winter 2025 presentation, the Italian designer showcased his signature pumps in more than 30 shades of suede, highlighting this classic silhouette for the upcoming season. Trendsetting ready-to-wear labels like Prada and Saint Laurent are also choosing elegant skinny-heeled pumps made from plush satin (Prada) and patent leather (YSL).
Another factor contributing to the resurgence of this style? None other than Angelina Jolie.
The Maria actress was seen outside Atelier Jolie—her New York City studio (which includes a boutique, customization workshop, and café) located on Great Jones Street in the former residence of artist Jean-Michel Basquiat—wearing an outfit characteristic of her style: a black suit over a white scoop-neck top, complemented by a Dior St. Honoré bag and Manolo Blahnik suede pumps. She is just one in a series of stiletto sightings this year, with more surely to follow. Scroll down to explore some of the most chic and timeless stilettos available.
Shop Our Favorite Chic Stilettos:
MANOLO BLAHNIK
Bb 90 Leather Pumps
Sharp, sleek, and effortlessly polished—these Manolos exemplify power dressing at its best.
MANGO
Asymmetrical Heeled Shoes
A sculptural heel at a high-street price? We're in love.
Minimalist yet eye-catching—these slingbacks pair well with anything.
CHRISTIAN LOUBOUTIN
Miss Z Patent Leather Pumps 100
Shiny patent leather meets all-day comfort—Parisian elegance in pump form.
JIMMY CHOO
Lotta 45 Leather-Trimmed Tulle Pumps
Simply genius! Delicate tulle and leather trim add the perfect romantic touch.
AQUAZZURA
65 Satin-Trimmed Ruched Tulle Point-Toe Pumps
Ballerina inspiration, elevated for the runway. Ethereal elegance at its finest.
Aquazzura
Passions Pumps 105
Sleek, sharp, and undeniably glamorous—these shoes are designed to catch attention.
MANOLO BLAHNIK
Bb 70 Canvas Pumps
The epitome of understated luxury.
GIANVITO ROSSI
Amelia 85 Patent-Leather Pumps
TOM FORD
Angelina Croc-Effect Leather Point-Toe Pumps
Power dressing in a stylish package.
DOLCE & GABBANA
Patent Leather Logo Pumps 90
The heel that speaks volumes—no accessories necessary.
CHRISTIAN LOUBOUTIN
Sporty Kate 85 Leather Pumps
An icon for a reason—flawless curves, a perfect point, and that signature red sole.
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