Harry Styles and Emily Ratajkowski set tongues wagging after they were spotted kissing while out and about in Tokyo this weekend as rumours circulate the supermodel may be the One Direction star’s new A List flame.
Singer Styles, 29, has been linked with several high profile partners since he was catapulted into the limelight on The X Factor in 2010, and has recently split with Hollywood beauty Olivia Wilde.
The photos of the singer kissing Ratajkowski in Japan may have poured cold water on rumours he is dating glamorous Australian model and fashion blogger, Yan Yan Chan.
Chan is a top international model who has starred in campaigns for the likes of high-end luxury fashion houses Louis Vuitton and Chanel. She is also friends with one of Styles’s former flames, Georgia Fowler.
Styles’s varied love life has seen him dating his director, as he was cast in Wilde’s film Don’t Worry Darling, and Xtra Factor presenter, the late Caroline Flack.
Harry Styles has been pictured kissing supermodel Emily Ratajkowski while the pair were out and about in Tokyo, Japan (pictured), but the 31-year-old model is not the only famous face the former X Factor contestant has been linked with over the years
He has also been spotted holding hands and kissing some of the world’s biggest stars, including supermodel Kendal Jenner and pop singer Taylor Swift.
Here, FEMAIL takes a look at Harry Styles’s varied romantic history…
Olivia Wilde, 39
Autumn 2020-November 2022
Styles and Olivia Wilde (pictured in London in March 2022) met on the set of Don’t Worry Darling after Styles was cast in a lead role and Wilde directed the project
Styles and Olivia Wilde met in September 2020 when he was cast in her film, Don’t Worry Darling. At the time, Wilde was engaged to her partner of around a decade, Jason Sudeikis, with whom she shares two children.
Two months after Styles was cast in the movie, Wilde and Sudeikis announced their engagement had ended. At the time the announcement was made, a source claimed the pair had been separated since the beginning of 2020.
People reported the source said: ‘[The split has] been amicable and they’ve transitioned into a great co-parenting routine. The children are the priority and the heart of the family’s relationship.’
As filming continued on set, Wilde heaped praise onto her lead actor in interviews, making note of his lack of ‘toxic masculinity’.
She said: ‘It’s pretty powerful and kind of extraordinary to see someone in his position redefining what it can mean to be a man with confidence.’
By January 2021, the couple were spotted out and about holding hands for the first time, as they dressed in all their finery to attend the wedding of Styles’s agent in Montecito, California.
The pair continued to date and grew closer over the next two years, with Styles reportedly meeting Wilde’s children as the relationship became more serious.
But in November 2022, just a few months after Don’t Worry Darling premiered in cinemas, the couple announced they were ‘taking a break’ from their relationship.
A source told People: ‘He’s still touring and is now going abroad. She is focusing on her kids and her work in L.A It’s a very amicable decision.’
Camille Rowe, 33
Summer 2017-July 2018
Styles dated French-born Victoria’s Secret Angel Camille Rowe for about a year between the summer of 2017 and 2018 (pictured together in New York)
Rowe (pictured) is rumoured to have been the inspiration behind some of the songs on Styles’s album Fine Line
Styles and Victoria’s secret model Camille Rowe dated for around a year between the summer of 2017 and July 2018.
Although the pair never publicly confirmed their romance, they were reported to have met through their mutual friend, Alexa Chung.
After their romance came to light, Harry and Camille were spotted on a string of sightings together, including a sushi date.
The French beauty also turned out to lend her support at a slew of his concerts, including one which she attended with her mother Anne Twist.
Following the couple’s split, Harry hinted during a promotional tour for his album Fine Line that some of the tracks on the record had been inspired by the romance.
Some fans suggested one of the lines in the song Falling hinted that Styles had been unfaithful to Rowe, referring to the lyrics: ‘I’m in my bed and you’re not here. And there’s no one to blame but the drink and my wandering hands.’
In another song, dubbed Cherry, Harry appeared to mock Camille’s new love interest art collector Theo Niarchos, whose father Philip owns an extensive collection.
Harry’s words on the song say: ”Don’t you call him ‘baby’, we’re not talking lately. Don’t you call him what you used to call me’, before adding: ‘Does he take you walking round his parents’ gallery?’
Tess Ward, 33
2017
Spot the difference: The pair were linked in 2017 and Tess appeared to fuel romance rumours by stepping out in the exact same Gucci shirt as the former X Factor star
Styles and food blogger Tess Ward reportedly shared a ‘whirlwind romance’ in 2017, with rumours of the romance flying when Ward was spotted wearing what appeared to be Styles’s shirt.
Despite keeping their romance under wraps, it appeared to be over before it had even begun as the pair soon decided to spend time apart.
A source told The Sun at the time: ‘Harry and Tess haven’t seen each other for a number of weeks.’
The insider added: ‘Tess realised she still had feelings for her ex after splitting from him to date Harry and has apologised to him for her romance with the singer.
‘She was in London this week and met her ex straight away — they’ve been inseparable since’.
Speaking to The Times during the time the pair were rumoured to be dating, Ward revealed she had been forced to delete several of her social media accounts, leaving her solely with Instagram, although she admitted she was beginning to resent that too.
She explained: ‘At the moment, I’m getting a lot of direct messages there, but I respectfully chose not to reply to them, because they’re all… interesting. I want a break!’
Dubbing the hate messages ‘very bizarre’, she reasoned: ‘I’m not the kind of person who’s interested in fame and if you’re put in an environment which you don’t understand and you can’t control and you don’t want, it’s horrible.’
Refusing to stoke the flames, when asked outright if she was dating Harry, Tess sighed: ‘I literally don’t have anything to say about that.’
Sara Sampaio, 31
2015
Victoria’s Secret Angel Sara Sampaio (pictured this month) was rumoured to have had a brief fling with Styles after they were spotted partying together in New York in 2015
Styles was rumoured to be dating Victoria’s Secret model Sara Sampaio in 2015 after the pair were spotted partying in Manhattan one evening, and pictured saying goodbye outside Sampaio’s hotel.
However, The Sun reported at the time that the Portuguese model later returned to the hotel, and emerged again the next morning around 11am, wearing the same clothes as the night before.
‘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,’ a source told the newspaper.
‘Sara left at 11am dressed exactly the same. Then Harry walked out at 11.15am and it looked like he’d been partying pretty hard.’
Georgia Fowler, 30
2015
New Zealand-born Victoria’s Secret Angel Georgia Fowler (pictured) sparked romance rumours with Styles when she posted a snap of the pair playing Scrabble
Another Victoria’s Secret Angel rumoured to have shared a romance with Styles is New Zealand-born model Georgia Fowler.
Fowler first sparked romance rumours with the singer after posting a sweet photo on her Snapchat page of Styles playing Scrabble with her, while dressed in a hoodie.
Little is known about the couple’s reported romance as they remained tight-lipped in public about their relationship, however Fowler did her best to shut down rumours one of the songs on Styles’s debut solo album was about her.
After fans buzzed around the lyrics to the song ‘Kiwi’, she was asked on Australia’s The Morning Show if the tune was about her.
The song features the curious lyric: ‘I think she said ‘I’m having your baby, it’s none of your business’.’
Presenter Kylie Gillies asked: ‘Harry Styles, on his album has a song called ‘Kiwi’, can you confirm or deny that it was named after you?’
‘Ah, don’t really know anything about it,’ Georgia shook her head, after referring to Harry as a ‘friend’
She quickly added: ‘Definitely don’t have a baby… that’s what the song is all about.’
Kendall Jenner, 27
2013, 2014, 2016
Styles had an on-again, off-again romance with supermodel and member of the Kardashian clan Kendall Jenner, with the pair first linked in 2012
Another of Styles’s whirlwind romances was with supermodel and member of the Kardashian family, Kendall Jenner.
The pair reportedly got close when Styles was 21 and Jenner was 18, but the long-distance relationship did not last.
After about three months of dating, a source told The Sun the pair had called time on their relationship.
At the time, Styles had already had a string of high profile relationships, however Kendall had reportedly only been involved with her high school boyfriend Julian Brooks.
A source told The Sun the pair had separated so they could focus on work and that there were no hard feelings between them.
They said: ‘There’s been no major fallout. They’re definitely still friends ad haven’t ruled anything out in the future.’
Despite calling time on their romance in 2014, the pair were spotted getting cosy on a yacht in St Barts early in 2016 after ringing in the new year together.
Photos showed the pair nuzzling into each other as they lay out on the sun deck surrounded by friends, who just passed by and didn’t distract them from each other for a second.
Shortly afterwards, the pair went their separate ways once again, but they appear to have remained friends as Jenner has been spotted at Styles’s concerts supporting her ex in recent years.
Taylor Swift, 33
2012
Styles was spotted out and about with singer Taylor Swift in late 2012 and early 2013 before the pair called time on their romance just days after ringing in the new year (pictured December 2022 in New York)
Between 2012 and 2013, Styles and singer Taylor Swift had a three month fling before the pair were reported to have split shortly after the new year following an ‘almighty row’.
Little more than a week after a very public display of affection on new year’s eve as the clock struck midnight to kick off 2013, a source confirmed to MailOnline that Styles and Swift had parted ways.
The source said: ‘Yes I can confirm they have split up. They were on holiday and had an almighty row. They are two young stars at the top of their game so who knows what will happen in the future.’
Swift, who is known to write songs about past relationships, is thought to have penned at least three songs about Styles – I Knew You Were Trouble, Style and Out of The Woods.
In 2015, the singer revealed her whirlwind romance with Styles had been an experience filled with anxiety.
During a performance at the Grammy Museum, she introduced Out of the Woods by telling the audience about her anxiety-inducing relationship – although she didn’t mention Styles by name.
‘I’m going to play you a song that I wrote about a relationship that I was in that the number one feeling I felt in the whole relationship was anxiety,’ she explained as she sat at her piano.
‘Because it felt very fragile, it felt very tentative. And it always felt like, “Okay, what’s the next road block? What’s the next thing that’s gonna deter this? How long do we have before this turns into just an awful mess and we break up? Is it a month? Is it three days?”‘
Caroline Flack, died aged 41 in 2020
2011
After meeting when Styles was a contestant on The X Factor and Flack was a host of spin-off show The Xtra Factor, the pair dated for three months (pictured in London in 2011)
Late TV presenter Caroline Flack met Styles when he was a contestant with One Direction on The X Factor and she was host of spin-off show The Xtra Factor.
With a 15 year age gap, as Styles was 17 and Flack was in her early 30s at the time, the couple saw their romance come under harsh criticism from outsiders which no doubt added to the decision to call time on their relationship after only three months.
However, the pair only ever had good things to say about each other and defended their romance in the face of criticism.
Following their split, the pair remained full of praise for each other, with Styles pouring cold water on rumours about the break up on Twitter.
He wrote: He tweeted: ‘Please know I didn’t “dump” Caroline. This was a mutual decision. She is one of the kindest, sweetest people I know.’
Caroline Flack sadly passed away in February 2020 after taking her own life.
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Read more at DailyMail.co.uk