Flats are beloved for a reason. Comfortable and easy, they're an obvious choice for a lot of occasions. But if you ask me, they'll never quite compare to a chic pair of stilettos or heeled boots when you want to take an outfit up a notch. And apparently, I'm not the only one who thinks so. More and more, celebrities are trading in their low-key flats for high-key heels, specifically ones with a certain '90s-inspired silhouette that look sharp every time (pun intended).
Spotted on supermodels like Kendall Jenner, Hailey Bieber, and Bella Hadid, as well as actresses from Anne Hathaway to Margot Robbie are spikey, pointed-toe heels of all types. Perfected by luxury labels like Balenciaga, Jimmy Choo, The Attico, and Prada and made accessible by brands like Mango, Zara, and H&M, these high-voltage pumps are making flats look less and less appealing by the day. So, whether you're dressing for a night out or looking to elevate a simple jeans-and-tee look, the 27 pairs ahead are just what you need.
On Hailey Bieber: Sportmax dress; Jimmy Choo heels; Balenciaga sunglasses
WHO: Bella Hadid
On Margot Robbie: Mango Check Wool-Blend Suit Waistcoat ($80), Structured Suit Blazer ($200), and Wool Suit Pants ($120); Prada Cleo Brushed Leather Mini Bag ($2600) and Brushed Leather Slingback Pumps ($1200)
On Anne Hathaway: Michael Kors Collection Balmacaan Crocodile Embossed Leather Coat ($3990), Leather A-Line Miniskirt ($1990), sweater; Christian Louboutin heels
On Kendall Jenner: Prada dress
Shop pointed-toe heels:
I can't get over how expensive these look.
Stuart Weitzman never misses in the boots department.
I've sent these to everyone I know. Literally everyone.
I just got these and feel like a million bucks when I wear them.
Sleek and sophisticated.
When BY FAR makes something, it becomes an instant trend.
Metallic shoes are the moment.
Extra sharp.
Prepare for compliments times 100.
These are giving Carolyn Bessette-Kennedy vibes.
Turn up the heat.
Everyone should own a pair of these.
The sleekest, shiniest heels a girl could ask for.
Fall is approaching.
Sale alert.
The sharpest of the bunch.
I can't believe I'm saying this, but sock boots are back in vogue.
Need.
In case you were wondering, these come in black too.
This price is going to be hard to beat.
Perfect for every occasion.
I'm in love. No really, I am.
The S/S 23 runways are bringing snakeskin back in a major way.
I might just need to buy these.
And while I'm shopping around, I need these too.
Just wow.
This brand is about to be huge.
Coming Up: Margot Robbie Made Mango Look Like Prada With This Chic Three-Piece Suit
-
Everyone in Paris Just Ditched Ankle Boots for This Boot Style That's Way More ElegantAnd super sleek.
-
*Not* Suede Boots: The Rich-Looking Boot Trend Fashion People Everywhere Are Wearing With Jeans and Skirts for Fall 2025You'll want to add a pair to your rotation.
-
*Not* Ankle Boots—the Rich-Looking Shoe Trend That's Quietly Taking Over for Fall 2025Shop the style inside.
-
The New Prada It Shoes for Fall 2025 Are Here, and They're Vintagey Cool-Girl HeelsAs seen on Lily James in NYC.
-
Black Boots Are Fine, But *This* Fall Shoe Color Trend Looks Rich as HellLily James is a fan.
-
I Spent Over an Hour BrowsingReplica Store's New Arrivals—34 Standout Fall Finds I Can't Stop Thinking AboutYou'll want to see these.
-
The Specific Way Everyone Stylish in NYC Will Be Wearing Boots With Jeans This FallIt's all about this styling trick.
-
Here They Are: The 6 Biggest Boot Trends of Fall 2025Exotic finishes! Sock boots! Western motifs!
