From Kendall Jenner to Olivia Dean: Harry Styles’ Complete Relationship History

During his time on X Factor, when One Direction were first put together, Harry dated the late Caroline Flack, who was then a presenter on The Xtra Factor.

A year later, and the boyband star was briefly linked to Australian model Emma Ostilly, who then appeared in One Direction's Gotta Be Yoooou music video.

The same year, and Harry was linked to Inbetweeners' Charlotte, AKA Emily Atack. It wasn't all too serious though, according to Emily, who said they were never official. Speaking about the dalliance in 2014, she said, 'We had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions.'

Remember Made In Chelsea's singing socialite Caggie Dunlop? Remember that Harry was briefly linked to her? Throwback!

Their romance might not have lasted very long, but it is definitely one of his most memorable - thanks to the paparazzi pics of their second date in New York's Central Park. Their split also inspired their music, as Taylor's Ready For It is reportedly about Harry, while many say Harry's Two Ghosts is about her, with the lyrics 'Same lips red, same eyes blue.' We'll let you decide.

Nicole was a guest judge on the X-Factor in 2010 when One Direction was formed - but, reportedly, the pair hooked up three years later.

The Keeping Up With The Kardashians star and Mr Styles were (first) linked in 2013. It also sparked a line of dalliances with Victoria's Secret models.

The pair were spotted at a pumpkin patch in 2014 - but the romance with the producer didn't last very long. At the time, there was a 12-year-age gap, with Erin being older.

Another VS model... Harry was spotted kissing the Portuguese model in New York back in 2015. (And Sara was spotted leaving Harry's hotel in the same clothes from the night before.)

New Zealand model Georgia - yes, another VS model - posted a video of the pair playing Scrabble online during their short lived romance. Some even believe that Harry's Kiwi is about her, because she's from NZ.

His romance with Kendall Jenner was reignited in 2016, with the pair dating for a year this time round. The pair are still on friendly terms, as can be seen from this cute pic of the former couple together at the 2019 Met Gala.

Harry reportedly dated the food blogger in 2017, but their romance is thought to have ended when she got back with her ex.

Another Victoria's Secret model, Camille and Harry dated for a year. Their break-up is thought to have had a big impact on Harry and it's believed to have inspired his second album, Fine Line. A voicemail from the French model was also included on track Cherry.

Say hello to 2021's most stylish couple: Olivia Wilde and Harry Styles. The pair appeared to confirm their romance at the beginning of the year by attending Harry's agent's wedding, where they were spied holding hands. It was said to be pretty serious at the time, and that Harry has met her kids, who she shares with ex Jason Sudekis. But as of November last year, the couple called it quits.

In a pixelated video that took the world by storm, model Emily Ratajkowski was spotted snogging Harry's face off under an umbrella in Tokyo back in March. While things never got serious between the pair, the kiss was enough to go viral. Addressing the rumours, Emily recently told Vogue Spain: 'It’s very bizarre to have certain experiences and then have the whole world know and comment on them.' True! But it was in the middle of the street...

Then came the rumour that Harry Styles is dating former Victoria's Secret model, Candice Swanepoel. Reports said the singer and the 34-year-old model were 'getting close', making her the seventh VS model he's been tied to. You can't say he doesn't have a type!

In June 2023, rumours that Harry was dating Canadian Bones and All actress and stage star Taylor Russell started swirling around, and were swiftly confirmed. The pair quickly became one of London and New York's most stylish couples, often praised for their his and hers styling. They also made sure to support each other's work, with Harry attending Lucy Prebble's play The Effect at the National Theatre, which earned Taylor rave reviews, and Taylor watching him on tour. They split up last May despite reportedly being pretty 'serious' .

Three months after his split from Taylor, there's speculation that Harry and singer Olivia Dean could be more than 'good friends' after they were seen at a branch of Five Guys in London. 'Harry and Olivia have known each other for a while. They have loads in common with their music taste and are enjoying getting to know each other out of the spotlight,' a source told The Sun. 'Harry loves nothing more than cycling and trying out new food spots in the capital and Olivia is a London girl so knows all the best places.' Olivia's profile rose this year after she was nominated for Best New Artist, British Artist of the Year and Best Pop Act at the Brit Awards.