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
-
Sporty, a Little Ugly, and Already on Elsa Hosk: Fall's First Viral Flats Have ArrivedPrepare to see them everywhere.
-
This Flat-Shoe Trend Makes Cropped Skinny Pants Look the *Most* Fall 2025PSA.
-
Forget the Sneakers—Baggy Jeans and a White Tee Look So Much Chicer With These Classic Fall ShoesLook polished without compromising comfort.
-
A Gen Z Fashion Person Just Told Me to Pass on Basic Loafers and Prioritize This Elegant Trend for Fall InsteadTake note.
-
The Chicest Fashion People I Know Wear These Anti-Trend Shoes Year-RoundClassic, elevated, and perennially chic.
-
If You Want to Freshen Up Your Shoe Collection, Start With These 33 Sneakers, Kitten Heels, and FlatsSending my apologies to your wallet.
-
It's Happening, People: These It Loafers From 1953 Are Back From the DeadReady or not.
-
Jeans, Flats, Jackets, and Sweaters—The Best of the Best In Each Category For FallMeet your new hero pieces.
