People With Cool Style Are Suddenly Wearing This Vintagey Heel Trend With Pants and Skirts

I'm well aware that we talk about flat shoes a lot here on Who What Wear, but let's take a break from that and talk about a heel trend I've been spotting as of late. It's a walkable heel style (as in, not a stiletto or a platform), it's pretty, and two women with cool style just wore it: Alexa Chung and Michelle Monaghan.
The heel trend I'm referring to is ballet pumps with an oversize bow. They look like something you'd stumble across in a vintage shop (and immediately buy if you get lucky with the size). Recently, though, the trend has been brought back into the spotlight by the creative director who’s arguably the most inspired by vintage designers in the game: Alessandro Michele. Michele is currently the creative director at Valentino, and he designed several oversize-bow ballet pumps for the brand's current collection.
Chung happened to wear a slingback pair with baggy black pants while in Cannes, while Monaghan was photographed in NYC wearing her tan leather ballet pumps with a denim midi skirt and red tank. I think we can all agree that the vintage-y heels look equally cool with both outfits.
Keep scrolling to shop the new celeb-approved heel trend for your wardrobe.
WHO: Alexa Chung
WEAR: Dôen top; Valentino pants, Valentino Garavani Nellcôte Small Shoulder Bag in Suede with Fringes ($2450), and Valet Du Roi Leather Slingback Flats ($990)
WHO: Michelle Monaghan
Shop Oversize-Bow Ballet Pumps

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
I'm Not Going to Mess Around—These Are the 3 Nordstrom Anniversary Sale Items I Can't Stop Thinking About (They Will Sell Out)
Some of my favorites are already gone.
-
I'm a Shopping Editor—These 5 Nordstrom Anniversary Sale Finds Are Living Rent-Free in My Head
Kitten heels, burgundy flats, and more.
-
If You Want to Look Like a Chic Fashion Person, Wear This Shoe Trend With Cropped Pants
Selena Gomez is on board.
-
Keep This Between You and Me: I Just Found a $165 Alt for The Row's Viral and Sold-Out $1300 Heels
You're welcome.
-
Did Foot-Jewelry Shoes Just Become the Biggest Trend of 2025?
Anklets and toe rings are on hiatus.
-
This Fall, Say Goodbye to Ballerinas Because This New Flat-Shoe Trend Is Taking Its Place
And it's even more sophisticated.
-
The Results Are In: These Are the Designer Shoes Dominating Summer 2025
Sneakers, sandals, and more.
-
Yeah, You *Have* Been Wearing Athletic Shorts With the Wrong Shoes This Whole Time
Here's the *right* way.
-
All Five Toes Are In—5 "Weird" Shoe Trends to Try This Summer
Chic foot pics loading here.
-
I Swear By Elegant Outfits—35 Standout Items That Would Fit Right Into My Closet
Here's to a chicer outfit rotation.