Harry Styles’ dating history: Taylor Swift, Kendall Jenner and more

A singer and actor who rose to stardom as part of the hit boy band One Direction, Harry Styles turned 30 on Thursday.

Styles was part of One Direction, a group formed in 2010 on the British TV talent show The X Factor, for six years. After the band announced it was going on an indefinite hiatus, he launched a solo singing career that has so far yielded three studio albums: Harry Styles (2017), Fine Line (2019) and Harry’s House (2022).

Styles has also accumulated a number of big-screen acting credits, appearing in major movies such as Dunkirk and Don’t Worry Darling.

The Brit’s professional achievements have certainly filled plenty of column inches; so too, has his love life, which has seen him embark on romances with several fellow celebs. As Styles celebrates a landmark birthday, we take a look back at some of his dating milestones.

Harry Styles’ dating history

Felicity Skinner

Before Styles shot to fame, he met and began dating Felicity Skinner, one of his earliest girlfriends. Then aged just 15, the couple were together for almost a year before going their separate ways. Looking back on the relationship in the years since they split, Skinner has said that Styles was a great boyfriend.

Caroline Flack

In 2011, Styles was linked to the British TV personality Caroline Flack, 14 years his senior. According to People magazine, the pair dated for several months, before breaking up in early 2012.

Emma Ostilly and Emily Atack

In April 2012, Styles was briefly rumoured to be going out with the American model Emma Ostilly. They were seen out and about together on several occasions.

The following month, reports surfaced that he was seeing the British actor Emily Atack, known for playing Charlotte Hinchcliffe on the successful comedy series The Inbetweeners. At the time, Atack insisted they were just “friends”; later, however, she admitted that their relationship had been a romantic one, albeit not serious.

Taylor Swift

Styles dated the American singer-songwriter Taylor Swift between October 2012 and January 2013. It’s rumoured that several Swift songs - “Out of the Woods”, “Style”, “All You Had to Do Was Stay”, “I Wish You Would”, “How You Get the Girl”, “This Love”, “I Know Places”, “Clean” and “Wonderland” - are about him.

Kendall Jenner

After splitting from Swift in early 2013, Styles was that November spotted on an apparent date with model and US reality-TV personality Kendall Jenner. However, neither Styles nor Jenner confirmed their romance. Two years later, the pair celebrated New Year’s Eve together.

They were also seen together several times in 2016, but People reported that September that they were not officially together.

Nadine Leopold, Georgia Fowler and Tess Ward

At the end of 2014 and the start of 2015, Styles was believed to be dating the Australian model Nadine Leopold. Per People, they went their separate ways in March 2015.

During autumn 2015, Styles briefly went out with the Kiwi model Georgia Fowler. In the wake of renewed talk of romance with Jenner, he then dated the British chef and blogger Tess Ward for a couple of months in mid-2017.

Camille Rowe

In July 2017, rumours began to spread that Styles was in a relationship with Victoria’s Secret model Camille Rowe. They were caught on camera together on a number of occasions, and Rowe was even seen at some of Styles’ concerts. They were snapped together for the final time in July 2018.

Olivia Wilde

In 2020, Styles met American actor and filmmaker Olivia Wilde, who cast him in her movie Don’t Worry Darling. In November that year, Wilde’s relationship with long-term partner Jason Sudeikis came to an end.

In January 2021, Styles and Wilde were snapped socialising for the first time, at a wedding in Montecito, California. Despite being spotted in each other’s company many times, with Wilde attending his concerts, they never publicly confirmed their relationship.

After almost two years together, they opted to call time on their relationship in November 2022, according to widespread reports.

Emily Ratajkowski

Styles was seen kissing Emily Ratajkowski in Tokyo in March 2023. However, his relationship with the American model was never serious.

Taylor Russell

After rumours of romance between Styles and Taylor Russell first began to surface in June 2023, the Canadian actor attended one of the singer’s concerts in Vienna a month later. In August, the pair were seen together at a London afterparty for the stage play The Effect, in which Russell appeared.

The following month, Styles and Russell were photopgraphed holding hands as they had a coffee in the UK capital, and in November they stepped out together to go to a U2 concert.