Harry Styles’ Dating History: Taylor Swift, Kendall Jenner and More

Harry Styles has accomplished a great deal since he rose to stardom as part of One Direction — and he’s had some very famous faces by his side along the way. One year after competing on The X Factor U.K., Styles had a brief relationship with Caroline Flack in 2011. He then started seeing Taylor Swift, but their romance was also short-lived. “I think relationships are hard enough, so I think you have to completely ignore everything from outside,” Styles exclusively told Us Weekly after his 2013 split from Swift. “If you have a lot of people from outside telling you what it is and they don’t even know you, telling you what your relationship is, that’s weird.” Styles has since been linked to multiple models, including Kendall Jenner and Emily Ratajkowski, and actresses Olivia Wilde and Taylor Russell. Scroll down to take a look back at Styles’ dating history:

Harry Styles has accomplished a great deal since he rose to stardom as part of One Direction — and he’s had some very famous faces by his side along the way. One year after competing on The X Factor U.K., Styles had a brief relationship with Caroline Flack in 2011. He then started seeing Taylor Swift, but their romance was also short-lived. “I think relationships are hard enough, so I think you have to completely ignore everything from outside,” Styles exclusively told Us Weekly after his 2013 split from Swift. “If you have a lot of people from outside telling you what it is and they don’t even know you, telling you what your relationship is, that’s weird.” Styles has since been linked to multiple models, including Kendall Jenner and Emily Ratajkowski, and actresses Olivia Wilde and Taylor Russell. Scroll down to take a look back at Styles’ dating history:

The Brits, who had a 14-year age gap, were in a relationship from 2011 to 2012. Styles tweeted at the time that their breakup “was a mutual decision,” calling Flack “one of the kindest, sweetest people I know.” The Love Island host died by suicide in 2019 at age 40.

Styles was spotted kissing the model in April 2012, but their fling never amounted to much.

The entertainers were famously photographed walking through Central Park in New York City in December 2012 on their second date. A month later, Swift broke up with Styles over an argument they had during a trip to the Caribbean. A source told Us at the time that the 1D member “said something he shouldn’t have.”

Styles and the Australian model were spotted together in Los Angeles several times from 2014 to 2015, but they never publicly spoke about their rumored romance.

The “Ever Since New York” crooner was seen hugging and kissing the Portuguese model in June 2015 after reportedly spending the night together at an NYC hotel.

After the New Zealand model shared a Snapchat video of her and Styles playing Scrabble together in October 2015, they had fans convinced that they were dating. Some people even speculated that the musician’s 2017 hit “Kiwi” was about Fowler, which she laughed off. “[I] definitely didn’t have a baby. That’s what the song’s all about, so I think it’s highly unlikely,” she said on Australia’s The Morning Show.

Us exclusively reported in May 2017 that Styles and the London-based food blogger were “casually seeing each other and [had] been on several dates” after meeting through mutual friends. They split just weeks later.

The Dunkirk star sparked dating rumors with the French model in July 2017 while attending a Fleetwood Mac concert in NYC. An eyewitness told Us at the time, “They looked really cozy. They seemed like they were having a good time and were enjoying each other’s company.” The pair dated for a year before calling it quits. Styles’ collaborator Tom Hull told Rolling Stone in August 2019 that the breakup “had a big impact on him.”

Styles was photographed holding hands with the actress, who directed him in the upcoming movie Don’t Worry Darling, at his manager Jeffrey Azoff’s wedding in January 2021 in Montecito, California. The news came months after Wilde and Jason Sudeikis called off their seven-year engagement.The two spent some time in Styles’ native London in April and then vacationed in Italy the following July.

"Olivia's really smitten by Harry,” an insider exclusively told Us after the couple were spotted packing on the PDA on a yacht off the Italian coast. “He makes her really happy. It's like he's brought out this giddy side of her. The thing that works for them is that they don't hide their relationship from the public. They don't care who's around watching them pack on the PDA.”

Us confirmed in November 2022 that the couple had split after less than two years of dating. 

Styles and the model were spotted packing on the PDA in Tokyo in March 2023. Prior to the rock star's split from Wilde, Ratajkowski had been seen with the Don't Worry Darling director at one of Styles' Paris concerts in July 2022. 

Styles was initially linked to the Canadian actress in June 2023 when they were seen out and about in London. The following month, Russell was spotted in the VIP section at Styles’ Vienna, Austria, concert. Russell was also in attendance for Styles’ final Love on Tour show in Italy in July 2023.

Us confirmed in August 2023 that Styles had been dating Russell “for a few months” and although it was “still new,” a source exclusively told Us, “Harry is always smiling when he’s with her.”

The pair were last seen publicly in September 2023 while on a stroll in North London. Us confirmed in May 2024 that Styles and Russell had split, with a source saying, “They’re taking some time to reevaluate things and see if this relationship is [one] that they really want to be in for the long run.”