The trendy way to style dress pants is by pairing them with this basic and these shoes.
Every now and then, a look that combines both comfort and style emerges, making it instantly worthy of imitation. This kind of ensemble revolves around achieving balance and skillfully contrasting casual items with more refined pieces. Thanks to Olivia Wilde, we now have an exciting new outfit formula to recreate. Recently, she was seen in fitted trousers paired with pointed-toe heels, adding a styling twist that hasn’t been widely considered—until now.
During a stroll in Los Angeles just before her appearance on Jimmy Kimmel Live!, Wilde wore a gray drawstring hoodie alongside her black trousers and black pointed-toe shoes. She opted to remove her black blazer in favor of lighter layers for the sunny weather, allowing her hoodie outfit to be showcased even more. I never would have thought to pair a hoodie with such luxurious pleated dress pants, but the proportions of her look were spot on. The hoodie was slightly cropped, sitting perfectly at the waistline of her trousers. She looked sophisticated, even with the sleeves of her hoodie casually scrunched up. This outfit has been on my mind consistently, and I felt compelled to share this brilliant yet simple styling tip with all of you.
On those days when you prefer not to overthink your outfit, consider recreating Wilde’s look. Keep scrolling to achieve her style and shop for more hoodies, dress pants, and pointed-toe heels that blend seamlessly with your personal aesthetic.
Spotted on Olivia Wilde
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
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