What’s not to love about Harry Styles? The former One Direction member is now an ultra-talented, ultra-successful solo musician, an actor, and a total heartthrob–which is why it’s no surprise that this Brit has had his fair share of reported flings and relationships. Of course, there’s a lot more to Harry than his dating history, but sometimes we just can’t help but wonder… Who has Harry Styles dated? And, um, do we have a chance?
That’s why we put together this list of (mostly) everyone the musician has been linked to over the years, from his controversial romance with Caroline Flack in 2011 to his most recent (and perhaps most serious) relationship with Olivia Wilde in 2022. Find it all below!
Who has Harry Styles dated?
From Taylor Swift to Kendall Jenner and all the Victoria’s Secret models in between, here’s a complete timeline of all of the lovely ladies Harry Styles has dated.
1. Caroline Flack - 2011-2012
A record deal isn’t the only thing Harry took away from the X Factor. The talent show is also where he met Caroline Flack, who was a presenter on The Xtra Factor (a bonus portion of the show that included behind-the-scenes interviews and unseen footage). She was also 14 years older than him, so their relationship caused quite the controversy. The public first caught wind of their romance when Harry was spotted leaving Caroline’s house, and she later confirmed the relationship in her autobiography. The pair split in January 2012 after a short three months of dating, upon which Harry tweeted: “Please know I didn’t ‘dump’ caroline. This was a mutual decision. She is one of the kindest, sweetest people I know. Please respect that.” The “Love Island” host died by suicide in 2019, and Harry wore a black rememberance ribbon to the BRITS shortly after.
2. Emma Ostilly - 2012
In April 2012, right around the time when whispers of a budding romance between Harry and Taylor Swift had started to spread, the One Direction member was photographed kissing American model Emma Ostilly in New Zealand. Whether or not this delayed Harry and Taylor’s official relationship, Emma and Harry didn’t seem to have a lasting one, as they weren’t spotted together again.
3. Taylor Swift - 2012-2013
After his fling with Emma, Harry and Taylor gave it a real go. The first real bits of evidence of their infamous relationship were photographs of them walking through Central Park together in December 2012, when Harry was 18 and Taylor was 22. Although the relationship lasted for just a few months, we got several fantastic pop songs out of it, including most of Taylor’s hit album 1989. (Hello, “Style”! Could it get more obvious?). The two even wore matching paper airplane necklaces, which Taylor references in “Out Of The Woods.” The power couple unfortunately split in January 2013, when a source told Us that Harry “said something he shouldn’t have.”
3. Kendall Jenner - 2013-2014, 2015-2016
After Taylor, Harry moved on to another high-profile girlfriend: Kendall Jenner. The pair was first linked together in late 2013 and split a few months later. However, they picked things back up in 2015 and spent New Year’s Eve together. Their second go-around lasted for nearly a year, and although they broke up in late 2016, they seem to still be good friends. They were photographed catching up at the 2019 Met Gala and even played a hilarious game together on The Late Late Show With James Corden, and she attended his concert in 2022.
4. Nicole Sherzinger - 2013
Those X Factor women just couldn’t stay away from this heartthrob! Nicole Scherzinger was a guest judge on the show when One Direction competed in 2010 (Harry was 19 and she was 35). Supposedly, they had a “dalliance” back then, and later the pair “hooked up over three years later when Harry had matured and was a member of the world’s biggest band,” according to a source from the Sun.
5. Nadine Leopold - 2014-2015
Throughout 2014-2015 Harry was spotted on multiple dates around Los Angeles with Australian Victoria’s Secret model Nadine Leopold. However, there’s not much information about their relationship besides a few photos of them together, so it’s safe to assume it wasn’t extremely serious or long-term. In fact, one source told HollywoodLife that the pair split because Nadine “wanted a more serious commitment from Harry.”
6. Sara Sampaio - 2015
Seems like Harry loves those models! In June 2015, he had a fling with yet another Victoria’s Secret Angel, Portuguese model Sara Sampaio. He was spotted Sara kissing in New York City, and the two had reportedly stayed in a hotel together the previous night. But this one doesn’t seem to have lasted long, either.
7. Georgia Fowler - 2015
Yes, another model–and another Victoria’s Secret Angel at that. In October of 2015, New Zealand model Georgia Fowler posted a video of the two playing Scrabble online, which seemed to confirm some sort of relationship between the two. Some fans think Harry’s song “Kiwi,” from his debut self-titled album, is about Georgia. However, she addressed this on Australia’s The Morning Showing by laughing and saying “I think it’s highly unlikely.”
8. Tess Ward - 2017
If you’ve been hoping for a break from the models on this list, we finally have something new to present: this time a writer (woo!). Harry was linked to food blogger Tess Ward back in 2017, but their relationship was kept mostly under wraps. The two reportedly met through mutual friends, according to a source who told Us that the they were “casually seeing each other and had been on several dates.” However, it only lasted for a few weeks.
9. Camille Rowe - 2017-2018
After Tess, Harry went right back to his roots and started dating French Victoria’s Secret Angel Camille Rowe. The pair were spotted together at a Fleetwood Mac concert in 2017, and their relationship lasted longer than his usual flings with models–they stayed together for a year. In fact, it’s suspected that many of the songs on Harry’s second album, Fine Line, are about Camille (and some of them are pretty dang sad, so we believe he was quite heartbroken). Tom Hull, a collaborator of Harry's, told Rolling Stone that his split from Camille “had a big impact on him.”
10. Olivia Wilde - 2021-2022
And how could we ever forget Olivia Wilde, Harry’s most recent (and one of his longest-term) relationships. After filming for Olivia’s movie starring Harry, Don’t Worry Darling, began, the two were photographed holding hands at Harry’s manager Jeffrey Azoff’s wedding in January of 2021. This was shortly after Olivia had split from her fiance Jason Sudeikis. Although Harry and Olivia got pretty serious (he spent time with her kids, and she came on tour with him!), they split in November 2022 after just under two years. The breakup followed some pretty serious drama surrounding Olivia and Sudeikis, but you can read more about that here.
Who knows what’s next?!
As you can see, Mr. Styles has quite the history when it comes to dating. From his long-term relationships to all those flings with models, one thing’s for sure: there’s been no shortage of beautiful women in his life. Which of his girlfriends was your favorite, and who would you like to see him date next? If you ask us, maybe it’s time he gives it a go with a fan.. But we’re biased.
