Ever since his humble beginnings in One Direction, fans have been obsessed with Harry Styles’ dating life.
And whilst he doesn’t shy away from writing about love – he does keep his private life out of the public eye.
Despite this, fans remain dedicated to keeping close tabs on his relationship history, and as the latest rumours swirl about his new potential match, we look back at every woman rumoured to have dated the famous singer.
Who is Harry Styles Dating?
Olivia Dean
Harry sent fans into a frenzy in August 2024 after he was spotted out and about with singer Olivia Dean.
The outing comes two months after he supposedly ended his relationship with Taylor Russel. The 30-year-old former One Direction member was spotted at Five Guys alongside the 25-year-old neo-soul singer.
“Harry and Olivia have known each other for a while,” a source reportedly told The Sun. “They have loads in common with their music taste and are enjoying getting to know each other out of the spotlight.”
“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.”
Who has Harry Styles dated?
Taylor Russell (2023-2024)
Harry Styles was linked to Canadian actress, Taylor Russell in June 2023. While the couple kept details of their relationship quiet, video footage showing the pair walking together went viral online.
According to TMZ, the 28-year-old actress was spotted at Harry’s show in Vienna in July, and also spotted walking around the city with the British singer.
In August the pair were spotted getting cozy on a date night in London according to TMZ, after Harry was spotted attending Taylor’s performance in The Effect at London’s National Theatre.
“It looked like they were holding hands,” an eyewitness told the publication at the time. “Harry stayed by Taylor’s side the whole time. He introduced her to James [Corden] and was whispering to her and laughing and smiling.”
“It looked like Taylor was on the phone to Harry when she left the theatre, telling him where to pick her up,” the source continued. “They are clearly trying to keep their romance under the radar and avoid being photographed together.”
In May 2024 The Sun reported the pair had split after 14 months together after a trip to Japan in April.
“Harry and Taylor have ended their relationship,” a source told the publication. “They went through a rough patch after their trip to Japan and are taking some time apart.”
“He’s been in America and she’s been in London. They made a lovely couple and it was obvious Taylor made Harry happy,” they continued.
“Things have become strained recently though and they’ve taken some time out.”
Olivia Wilde (2021-2022)
Olivia Wilde and Harry Styles were photographed holding hands at a friend’s wedding in January 2021. The relationship came almost a year after it was announced that Harry would replace Shia LaBeouf in Olivia’s film, Don’t Worry Darling.
Throughout their 18-month relationship, Olivia was regularly spotted at his concerts, however, the pair called it quits in November 2022, with a source telling People that Harry’s tour schedule was to blame.
In July 2023, over six months after the pair’s decision to split went public, Harry was spotted with an interesting new tattoo. One word: Olivia.
Is it new? It it about his ex-flame? A tribute to the One Direction song Olivia? We need answers!
Emily Ratajkowski (March 2023)
Footage emerged of Harry making out with model, author and podcaster Emily Ratajkowski – aka Emrata – on the streets of Tokyo in March 2023. The two did not appear to be bothered by onlookers as they shared a smooch up against a car.
The footage came after the model was linked to Eric Andre after finalising her divorce from Sebastian Bear-McClard in September 202 – and despite the highly publicised video, it appears Harry and Emily’s chemistry fizzled out, with the pair not spotted together again.
Yan Yan Chan (January 2023)
Womans Day reported on the possible new relationship between Harry and Aussie influencer Yan Yan Chan, 28.
The pair, who have followed each other on Instagram since 2020 have “known each other for a while,” an insider told the publication.
According to the source, Harry, 29, “loves keeping good company while he’s away from home” and Yan Yan “by all accounts is a lot of fun”.
Camille Rowe (2017-2018)
Harry Styles and French model Camille Rowe dated for around a year. Following their split, Harry released the track ‘Cherry’ which features a recording of her voice.
Townes Adair Jones (2017)
In 2017, college student Townes Adair Jones was set up on a blind date with Styles by her actress sister and the rest is history. Although not much is known about the relationship, Harry’s song ‘Carolina’ is a reference to her hometown.
Tess Ward (2017)
Food blogger Tess Ward was linked to Harry Styles after the pair were spotted driving together in 2017. The blogger fuelled rumours after fans spotted her wearing what looked to be Harry’s Gucci shirt in an Instagram post.
Georgia Fowler (2015)
Although there was no hard proof that Harry and the Victoria’s Secret model dated, many fans believe the couple were the real deal. Why? Because Harry’s song ‘Kiwi’ was thought to be linked to the New Zealand model.
Kendall Jenner (2015)
Just friends or so much more? Kendall Jenner and Harry Styles were the subjects of speculation often throughout the years. Whilst the rumours began in 2013, photos emerged of them kissing in 2015, with Kendall’s sister, Khloe confirming the relationship.
Although the relationship was short-lived, the pair remained friendly and are often photographed at events together.
Nadine Leopold (2014-2015)
Another Victoria’s Secret Angel! Harry Styles was briefly linked to Austrian model Nadine Leopold following multiple sightings of the pair together.
Cara Delevingne (2012)
Although there was no confirmation of this couple, multiple media publications reported that Cara and Harry were dating in 2012, and Harry was regularly spotted sitting front row at the British model’s runway shows.
Taylor Swift (2012)
Whilst it may have been a whirlwind romance – fans will never forget when Harry and Taylor dated. Although the relationship only lasted a few months, it resulted in some iconic tunes. “I Knew You Were Trouble,” “Out Of The Woods” and “Style” are all rumoured to be about Harry.
Emily Atack (2012)
Harry was also linked to Inbetweeners star, Emily Atack in 2012. Although the pair were never officially a couple, the actress did later confirm their romance, telling Huffington Post “we had a short lived thing that was just a bit of fun.”
Emily Ostilly (2012)
Emma Ostilly, the star of the music video for the One Direction song, ‘Gotta Be You,’ was pictured kissing Harry Styles in 2012, but the relationship was short-lived.
Caroline Flack (2011)
Harry was briefly linked to the late presenter, Caroline Flack however their short-lived relationship was marred with controversy due to their age difference. Harry was 17 and Caroline was 31.
