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An ex’s t-shirt is a common relic left over from relationships that didn’t work out, but as she was out and about in Los Angeles on June 20, 2023, a certain item of clothing led some fans to speculate if Harry Styles and Olivia Wilde are back together after splitting late 2022.
On November 18, 2022, People reported that the “As It Was” singer and the Booksmart director had called it quits after two years of dating and multiple sources confirmed to the outlet that the two were “taking a break.” The ex-couple confirmed their romance in January 2021 after they attended Harry’s manager Jeffrey Azoff’s wedding together in Montecito, California, where Styles referred to Wilde as his “girlfriend” in his wedding speech, according to Us Weekly. “Taking a break” might be the key phrase, there, because fans have pointed out that she’s still subtly interacting with him on Instagram. Harry’s sister Gemma Styles shared a video from his Love On Tour show in London on June 16, 2023, Olivia gave it a “like”. One Twitter user with legit receipts pointed out: “Harry is looking at Olivia on Insta, Olivia is liking Gemma’s post about Harry (something she hasn’t done in over a year)… maybe there’s hope for them yet.” There’s another clue that has sent fans into a spiral wondering if Harry Styles and Olivia Wilde are back together.
We’re just going off some fan speculation here but it’s clear things are, at least, still amicable between them. On Tuesday, June 20, 2023, Olivia was spotted wearing a Space Fruity Records, a Beijing-based record label, t-shirt while out and about in LA—nursing, by the way, the BIGGEST water bottle I have ever seen.

It’s the same t-shirt Harry wore when he went to see Ariana Grande perform in London in 2019 (see a fan pic here) and, while you can buy replicas online, the one Liv’s sporting looks well-worn. Of course, this is no finite indication that they’re back together. As mentioned, exes hold onto each other’s things all the time (I doubt I’ll ever see my Lord of the Rings director’s cut DVD box set ever again—live and learn) but it certainly got fans talking.
08/17/19 | Harry wore a Space Fruity Records t-shirt at the @ArianaGrande show in London. It's a record label started by the owners of fRUITYSPACE record store in Beijing.
— Harry Styles Fashion Archive (@hsfasharchive) August 17, 2019
1. https://t.co/7lBMJAGdK9
2. https://t.co/QkSB14eaqC pic.twitter.com/EOtP3VJx19
Since the news of their split broke, people close to Olivia and Harry have been providing reasons for their relationship breakdown. “The public pressure on them has been difficult,” a friend of the ex-couple told People. “They’ve had ups and downs throughout the relationship.” The main tabloid allegation that revolved around the ex-couple was that Olivia cheated on her then-fiancé Jason Sudeikis with Harry while filming her second directorial project. The two started dating on the set of their movie Don’t Worry Darling where Olivia directed and Harry starred. At the time, Olivia was still engaged. Olivia and the Ted Lasso star were together from 2011 until November 2020. The couple got engaged in 2013 and share two children together: Otis and Daisy.

Olivia talked about how the ongoing rumors of her relationship affected her in a Vogue profile. “It’s obviously really tempting to correct a false narrative,” she said. “But I think what you realize is that when you’re really happy, it doesn’t matter what strangers think about it. All that matters to you is what’s real, and what you love, and who you love.”
She finally put the cheating rumors to rest when she described it as “complete horse shit” in a Vanity Fair cover profile. “Our relationship was over long before I met Harry. Like any relationship that ends, it didn’t end overnight. Unfortunately, Jason and I had a very bumpy road, and we officially dissolved the relationship towards the beginning of the pandemic,” she said at the time. “We were raising two kids during lockdown, so we co-parented through that time. Once it became clear that cohabitating was no longer beneficial for the children, it became the responsible thing to NOT, because we could be better parents as friends who lived in different houses.”
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