Harry Styles has dated a string of well-known names since he catapulted to fame on The X Factor in 2010.
Watermelon Sugar hitmaker Harry, 26, has never been afraid to share his penchant for dating older women and he previously shared that he’d date someone as old as his mum – but that was the furthest he’d push an age gap.
The One Direction star is most-recently linked to actress Olivia Wilde – 10-years his senior – after the genetically-blessed pair were pictured holding hands as they attended a wedding together.
As lothario Harry appears to embark on his new romance with House name Olivia, here is a look the boyband sensation’s list of former flings including the late Caroline Flack, songstress Taylor Swift and a string of Victoria’s Secret models.
Harry met TV presenter Caroline when she co-hosted The X Factor sister show The Extra Factor.
The singer was 17 at the time and Caroline – who tragically took her own life aged 40 in 2020 – was 31 but that did not stop the duo falling madly in love.
According to reports, Harry and Caroline’s romance blossomed after he told her about his feelings at an X Factor party at the W Hotel in London in October 2010.
Things quickly turned serious, with Harry taking Caroline home to Holmes Chapel to meet his mum Anne Twist – who was a big fan. Meanwhile, he reportedly met the Flack family who ‘fully approved’ of their relationship.
Caroline apparently put the brakes on their relationship just before Christmas and Harry was said to have been devastated.
The pair reunited in January 2012 but three-months later they ended their relationship for good – ahead of him heading to America to tour with One Direction.
And after they went their separate ways he urged his fans to leave Caroline alone when he defended the TV star in a chivalrous post.
He typed at the time: “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.”
In May 2012 it was rumoured Emily Atack and Harry were dating, although she did not confirm it at the time.
Then in August 2013, The Inbetweeners star admitted: “Yeah, we had a short-lived thing. But we were never boyfriend and girlfriend.
“Harry and I had fun, then went in opposite directions. We haven’t spoken in a while.”
After his fling with Emily, Harry moved onto another blonde as he started dating chart-topper Taylor Swift.
The pair were together for a year but when they decided to end their romance the One Direction star, who was 19 at the time, described his relationship with Taylor as “a huge pain in the a**e”.
Taylor went on to write a song called Out Of The Woods on her album 1989 – which is thought to be about her and Harry’s courtship.
Swift told US mag Rolling Stone that the revealing track is a frantic tale of a relationship where, she says, “every day was a struggle. Forget making plans for life – we were just trying to make it to next week”.
Taylor has since moved on with British actor Joe Alwyn, who she has dated since 2016.
Harry reportedly had a brief romance with Nicole Scherzinger, it has been claimed.
According to The Sun newspaper, Harry was 19 when he started texting Nicole.
A source said,at the time: “They had a dalliance at the end of the X Factor in 2013 and met up again early last year.
“Harry was obviously very taken by Nicole who is stunning and he had always looked up to her.
“She was a guest judge on X Factor at the time One Direction were formed and has always claimed credit for putting the band together, even though Simon Cowell says it was his idea.”
A pal of Nicole’s claims the pair snogged and got on well together but never dated.
Harry and Keeping Up With The Kardashians star Kendall Jenner were first linked in November 2013 when Harry, who was still with One Direction at the time, revealed they’d been out for dinner.
Things moved quickly and Harry was spotted outside her hotel in London just weeks later before they saw in the New Year on a romantic ski trip.
But by London Fashion Week the following February, rumours were swirling that it was all over.
That was until 2016 when Harry popped up aboard Kendall’s luxury yacht off the Caribbean island of Anguilla, where they were pictured getting hot and heavy.
According to reports, the pair even went on to holiday in St. Barts with Kris Jenner, her boyfriend Corey Gamble and Harry’s mother Anne Cox.
At the time, Kendall’s big sister Khloe Kardashian opened up about her relationship status, telling Entertainment Tonight: “Do I think they’re dating? Yes. I don’t know if they’re, like, boyfriend-girlfriend. Nowadays I don’t know. People are weird with stuff. So, I don’t know their title.
“But I mean, they were in St. Barts together hanging out, so to me that’s dating. I would call that dating. [But] I don’t know what they are. You know, you have the have ‘the talk’ [and] I don’t know if they’ve had that talk yet.”
Harry and Erin Foster were rumoured to be dating in 2014 after the Daily Mail reported that the daughter of David Foster and the songwriter visited a pumpkin patch.
It is thought they met through a mutual friend.
Next, Harry was thought to be getting close to Victoria’s Secret model Nadine Leopold between 2014-2015.
Sources claimed at the time that Harry was so besotted with Nadine that he had her initials tattooed on him.
A source told the Daily Star newspaper: “Harry made everyone sign confidentiality agreements so the girl’s letters are a secret at the moment.
“But he had two sets of initials together – ‘HS’ is one of them of course, but everyone’s saying that the other initials are ‘NL’ – for Nadine Leopold.
“Harry used to go to tattoo parlours when he came to LA. But he gets mobbed so much that he has an artist go to his house instead.”
Nadine reportedly dumbed Harry as she wanted more commitment.
A source dished to Hollywoodlife.com: “Nadine wanted a more serious commitment from Harry.
“She felt like he needed to make more of an effort to see her. She just didn’t feel like he was taking their relationship seriously enough, and basically, she doesn’t have time for any games in her life.”
Harry then moved onto another Victoria’s Secret model by hooking up with Sara Sampaio.
The rumour mill began after the duo spent the night partying with Portuguese stunner Sara Sampaio at New York’s Ludlow Hotel in 2015.
Snaps captured featured Harry hugging the Angel as they say goodbye outside the hotel before he went back to the bar to carry on drinking.
But according to sources, the brunette later returned to continue partying and the pair left the hotel on Friday morning within 15 minutes of each other.
A source said: “Harry had been partying with a group of friends at the Ludlow but seemed very friendly with Sara. There was definitely chemistry there as they hugged and kissed each other when she left.
“But everyone thinks something was up as she came back and they left so soon after each other the next morning.
“Sara left at 11am dressed exactly the same. Then Harry walked out at 11.15am with his hair up in a bun on his head. It looked like he’d been partying pretty hard.”
Harry was then linked to another lingerie model after the heartthrob featured on Georgia Fowler’s social media whilst they played a cosy game of Scrabble in 2015.
An insider said at the time: “Harry is very careful about who he spends time with, so Georgia must be very special for him to allow her to share their moment with her followers.”
In the video, Harry can be seen leaning over a Scrabble board in his nightwear as he puts his letters down and laughs to himself.
Harry then moved on in 2017 with food blogger Tess Ward.
The pair are believed to have met through mutual friends but their romance was uncovered when eagle-eyed Twitter users spotted the chef was wearing one of Harry’s T-shirts.
The pair are said to have enjoyed a number of low-key dates after being introduced by mutual pals.
Friends close to the singer, said he’s really fell for the blonde, who is the author of The Naked Diet and The Naked Cookbook.
“As soon as Harry met Tess there was an instant spark between them,” a source said.
They added to The Sun: “They really bonded over their mutual love of quirky fashion and food – and things turned romantic quickly.
“They’ve been on a number of dates while Harry has been in London and he’s already introduced Tess to some of his close friends including his personal stylist Lou Teasdale.”
The blogger and musician’s whirlwind romance apparently ended when Tess decided to rekindle a flame with her former boyfriend, according to The Sun.
Victoria’s Secret model Camille Rowe was the next lady on Harry’s love list.
The hot pair were spotted together at a gig in New York in Augst 2017.
“Harry and Camille are in the early stages of dating. He’s very protective of his relationships so isn’t going to want to make a big show of things. They are well suited and seem happy,” a source told The Sun.
“She’s a real star on the rise. He seems besotted.”
According to a report in The Sun, their romance collapsed after 12-months due to their busy schedules.
Olivia Wilde is the latest woman to be linked to Harry.
At the weekend, Harry was seen heading to his agent Jeff Azoff’s wedding to bride Glenne Christiaansen in California, hand-in-hand with Olivia.
House star Olivia, who has two children with her ex Jason Sudeikis and was previously married to Tao Ruspoli, looked stunning in a floor-length floral dress.
It’s said that they grew close on the set of their new movie Don’t Worry Darling, which Olivia is directing.
She’s also said to be starring in the film alongside Harry.
Before heading to the wedding, they were pictured arriving at Harry’s house in Los Angeles with luggage.
But they left fans stunned when they arrived at the wedding holding hands, seemingly confirming their romance.