Olivia Wilde Wore the Best Flats Trend to Pair With Cropped Pants

Olivia Wilde's casual California-girl style is often very casual—as in she wears leggings a lot. (It's worth noting that the paparazzi clearly camp out at her gym on a regular basis.) But while out with friends a few days ago in L.A., Wilde traded leggings for a pair of cropped pants, which she paired with an oversize striped button-down shirt and a crossbody Saint Laurent bag. But of course, I'm here to talk about her shoes.
If you're looking for a way to make cropped pants or jeans look fresh, look no further. The flats trend Wilde wore is a great success with cropped pants. That trend is chunky loafers, the shoe style that celebrities can't get enough of (Hailey Bieber and Katie Holmes among them) and has become a staple in most fashion people's closets.
While loafers of all types are cool right now, it's chunky styles that undoubtedly give the most trend-forward edge to an outfit, cropped-pant outfits included. Scroll to shop the current pairs that I think are the chicest in case Wilde has unknowingly influenced you.
On Olivia Wilde: Saint Laurent Loulou Puffer Toy Bag ($2290)
Shop Chunky Loafers
Next up, 5 Pairs of Flats a Stylist Says Go With Everything

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.
-
9 Top, Jeans, and Shoe Outfit Combos That Fashion People Will Be Wearing This Spring
I plan to re-create these ASAP.
By Jennifer Camp Forbes
-
It's True—Fashion People Are Ditching Their White Sneakers For These More Elevated Shoe Trends
I'm following suit.
By Humaa Hussain
-
10 Spring Outfit Ideas That Will Make Anyone Look Like a Fashion Person
Bring on the compliments.
By Jennifer Camp Forbes
-
Re: Your Ballet Flats—Here Are the Chicest Ways to Wear Them This Summer
Because we know you're wondering.
By Michelle Scanga
-
It's Here: 2025's Most (Unexpectedly) Elegant Flat-Shoe Trend
It works with everything.
By Nikki Chwatt
-
Style Rut? I Have Something for That—33 Stellar Spring Picks From Nordstrom, Zara, and Madewell
I see chic outfits in your future.
By Jennifer Camp Forbes
-
I Just Ran to My Computer to Track Down Jennifer Lawrence's Trendy Flats
That didn't take long…
By Allyson Payer
-
Try Any of These 5 Spring Shoe Trends, and You Won't Be Able to Stop Staring at Your Feet
I'm obsessed.
By Jennifer Camp Forbes