Now and then, an outfit that is equal parts comfortable and chic comes out and becomes instantly copy-worthy. This type of outfit is all about balance and the art of juxtaposing casual pieces with elevated ones. Thanks to Olivia Wilde, we have an exciting new outfit formula ready for you to re-create. Wilde recently wore trousers with pointed-toe heels and added a styling twist that not many have thought to do—until now.
On a walk in L.A., right before her appearance on Jimmy Kimmel Live!, Wilde was spotted wearing a gray drawstring hoodie with her black trousers and black pointed-toe shoes. She slipped off her black blazer in favor of lighter layers for the sunny day and revealed her hoodie-outfit details even more. I wouldn’t have thought to style a hoodie with such luxe pleated dress pants, but the proportions of her outfit were perfectly placed together. Her hoodie was slightly cropped, hitting right at the waistline of her pants. She looked polished, even with a hoodie scrunched at the arms casually. This look has been living rent-free in my mind, and I couldn’t help but share this genius yet easy styling trick with all of you.
On the days you don’t feel like overthinking your outfit too much, try re-creating Wilde’s outfit. Keep scrolling to get her look, and shop more hoodies, dress pants, and pointed-toe shoes that blend well with your personal style.
Spotted on Olivia Wilde
(Image credit: PG/Bauer-Griffin/GC Images)
Get the Look
ZARA
Basic Hoodie Sweatshirt
The Frankie Shop
Ripley Pleated Trousers
Tony Bianco
Stevie Black Vintage Pumps
Prada
55mm Pillow Sunglasses
Shop More Hoodies
Reformation
Austin Zip Up Hoodie
SKIMS
Cotton Fleece Blend Classic Hoodie
Le Bop
Cleo Pullover Hoodie
Shop More Dress Pants
PISTOLA
Eden Pleated Ponte Trousers
ALL THE WAYS
Francesca Pants
COS
Pleated Cotton Barrel-Leg Trousers
Shop More Pointed-Toe Shoes
Schutz
Lou Pointed Toe Pumps
Khaite
Jett Patent Leather Stiletto D’orsay Pumps
Calvin Klein
Roxanna Pointed Toe Pumps
Tory Burch
Double T Buckle Pumps 80mm
Explore More:
:quality(85):upscale()/2025/05/15/715/n/1922564/ab90e60a682611e7f06d97.77199685_.png "12 Free People Summer Must Haves in a Shopping Editors Cart")
:quality(85):upscale()/2026/06/12/673/n/1922564/007836996a2c211b8b6222.27413131_.png "10 Fathers Day Gifts at Tecovas, From Bestselling Boots to Elevated Basics")
:quality(85):upscale()/2026/06/09/732/n/49352476/33700b5b6a28408346cd80.35100877_.png "Timothée and Kylie Are the Best Dressed Courtside Couple – Shop Their Looks From")
![[Review] On the Trail of UFOs: The Disclosure Era – Episode 1](https://ihorror.com/wp-content/uploads/2026/06/C9431.MP4.04_18_00_19.Still001-1024x576.jpeg "[Review] On the Trail of UFOs: The Disclosure Era – Episode 1")
