Olivia Wilde Wore the Perfect Anti-Skinny Jeans to Pair With a Button-Down
If you told me that I could only borrow clothes from Olivia Wilde's closet, I wouldn't make a fuss. Time and time again, Wilde proves that she has an impressive collection of elevated basics that strike the perfect balance between aspirational and accessible, classic and contemporary. Don't believe me? Take a look at her most recent off-duty outfit, which consisted of luxe, relaxed, and well-cut pieces that made her look timeless and utterly of the moment.
Yesterday in New York, Olivia Wilde put together a laid-back and effortless outfit. She wore flowy wide-leg pants and an oversized button-down shirt featuring a popular summer print: stripes. To complete her look, she opted for Adidas Samba sneakers, a canvas tote bag, and her go-to Ray-Ban Wayfarer sunglasses.
On Olivia Wilde: Balenciaga Oversize Stripe Button-Up Shirt ($995); Adidas OG Samba Sneakers ($100); Ray-Ban Original Wayfarer Sunglasses ($180)
This isn't the first time Wilde has advocated for leaving skinny jeans or tight-fitting pants at home. Other than being spotted in workout leggings, the actress has been seen several times in the last few months wearing baggy straight-leg and cropped silhouettes, which are undoubtedly the comfiest looks to run your errands in. On each occasion, she's paired her pants alongside lightweight coats, like blazers and denim jackets, and practical footwear, such as retro-inspired sneakers.
Scroll on to shop Wilde's look and more anti-skinny pants, which look amazing with button-down shirts or any top style.
Shop our favorite anti-skinny jeans
Dark-hued jeans are set to take off this fall because they're versatile and elegant.
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Who What Wear editors are so into crisp khaki pants right now.
These pair well with ballet flats and kitten heels.
The infamous Cary Jeans are elite with their perfect blue wash and a super-relaxed fit.
Banana Republic offers a fantastic range of stylish tailored pants that combine top-notch quality with wallet-friendly prices.
Linen pants will always be forward—especially when they feature a pin-tuck and a mid-rise fit.
Nikki Chwatt is an associate fashion editor based in New York City. She joined Who What Wear in 2024 after writing fashion, beauty, and lifestyle content for WWD, Well+Good, Editorialist, and more. With a passion for personal style and the creativity that comes with it, one of Chwatt's goals is to help others understand that there is no such thing as a “good” or “bad” style; it’s just about putting an outfit together that makes you feel confident in yourself. When she's not writing, you can find her taking a Pilates class, reading a powerful romance novel, or exploring a new wellness spot in Manhattan.
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