Two topics, in stark contrast with each other, have dominated recent news cycles: America’s startling political divide and, of course, that photograph of Olivia Wilde (36) and Harry Styles (26) holding hands (whilst both wearing Gucci). Yes, it would appear young Styles caught Wilde’s tenure on House, M.D. back in the day and thought, “just what the doctor ordered.”
Following Wilde’s split from funnyman Jason Sudeikis, Styles and the actress have gone public with their relationship since meeting on the set of Don’t Worry Darling. Kudos. Nothing could be more uplifting than two beautiful people (with impeccable taste in fashion) getting together, saving money, and pulling from the same closet. Or at least we have to assume that’s part of the appeal. The couple has certainly worn similar outfits over the years, prompting us to do what is timely, relevant, and overtly necessary—pit their fits against one another.
Cover Photo: BACKGRID
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If we’ve proven anything, it’s that the sartorial elegance of Wilde and Styles is more than compatible. She may have been doing it longer but he’s been doing it better. Like all good things, this battle was perfectly balanced. Look good, feel good—these (alleged) pillow pals look way too happy.
Overall Winner: Wyles (Tie)
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Olivia Wilde v Harry Styles
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Here for Sheer
She wore it to The Late Show With Stephen Colbert in 2017 and he tipped his proverbial hat to her defying gender norms with it at 2019’s Met Gala. It’s bold, beautiful, sheer, and we’re here to see it thru.
Winner: Styles
Photo: James Devaney/Sean Zanni (Getty Image)
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Wearing Stripes with Plaid Comes Easy
Albert Einstein said, “Once you can accept the universe as matter expanding into nothing that is something, wearing stripes with plaid comes easy.” Existential angst is a plight regularly conquered for these two. However, while Wilde had the forethought to color coordinate with the venue, Stiles looks like he’s wearing a brand new (and very trendy) dishrag.
Winner: Wilde
Photo: Phillip Faraone/Neil Mockford (Getty Images)
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Flexing the Floral
The term “flower power” originated and revolved around the symbolic action of protesting against the Vietnam War (by handing out flowers to policemen). What does that have to do with these love birds? Maybe nothing. Maybe something. Regardless, Styles rocked the swagger of a Jackson Pollock painting back in 2015 and, four years later, Wilde followed suit (literally).
Winner: Styles
Photo: Matt Winkelmeyer/Jason Merritt (Getty Images)
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Blue Power Suits
Is that corduroy? Sorry, Stevie Nicks.
Winner: Wilde
Photo: NBC/Kevin Mazur (Getty Images)
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The Hat
Frank Sinatra: “Cock your hat – angles are attitudes.” Styles looks like an Elmore Leonard protagonist; a man of God who’s also down with hedonism. These two will totally be swapping hats.
Winner: Styles
Photo: Jon Kopaloff/FilmMagic/Rich Fury (Getty Images)
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The White Pearl Necklace
Innuendos aside, Styles’ bit of embroidery and wannabe pearls pale in comparison to Wilde’s retro spread for Abercrombie & Fitch—where she’s presumably sporting the full-fledged real deal.
Winner: Wilde
Photo: 2004 Abercrombie & Fitch/Dia Dipasupil (Getty Images)
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Wearing a Bow Tie is a Statement
If presented with Styles' red bow tie, Pee-wee Herman would be beside himself.
Winner: Wilde
Photo: Ray Tamarra (Getty Images)/Splash News
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Suit and Tie? Gown and Jacket
It takes balls to wear a dress on the cover of Vogue.
Winner: Styles
Photo: Steve Granitz/WireImage/Vogue December 2020
