The Cool-Girl Way to Wear Dress Pants Is With This Basic and These Shoes
See how Olivia Wilde styles it.
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.
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Kerane Marcellus is a New York-based writer. She joined the Who What Wear team in 2025 after writing for Essence Magazine and freelancing for a number of other arts and culture publications. Fashion is a form of expression that she encourages everyone to take part in. There is no right or wrong in getting dressed! When she's not writing, she's reading in the park or gallery hopping in the city.