Harry Styles’ Dating History Proves He’s a True Romantic: See the Full List of His Ex-Girlfriends

Caroline Flack

Harry and the late Love Island host dated from 2011 to 2012 — and had a controversial 14-year age gap — but parted ways mutually. He called Caroline “one of the kindest, sweetest people I know” on Twitter following the split. She died by suicide in February 2020 at age 40.

Emma Ostilly

The boyband alum started dating the model after meeting her on the set of One Direction’s “Gotta Be You” music video. They were spotted kissing in April 2012 — but, ultimately, things fizzled out quickly.

Taylor Swift

Harry and the pop icon were famously photographed holding hands amid a Central Park stroll — their second date — in December 2012. The following month, the former flames split over an argument they had had while vacationing in the Caribbean.

There have long since been rumors that Taylor’s songs “Style” and “Out of the Woods” were written about Harry, while his song “Two Ghosts” was supposedly written about the Tennessee native. Taylor’s 2023 vault song, “Is It Over Yet?,” is believed to be about the end of her romance with Harry. She seemingly references a woman Harry dated after her with the line, “Your new girl is my clone.”

Kimberly Stewart

Model and actress Kimberly reportedly dated Harry in April 2013, three months after his romance with Taylor ended, although the two never confirmed their relationship. At the time, he was 19 years old, while Kimberly was 33.

Kendall Jenner

Harry accompanied the Keeping Up With the Kardashians star on a ski trip with her family in 2013, which sparked romance rumors. In January 2016, the pair really turned heads when they were photographed canoodling on a yacht in St. Barts.

They reunited at the 2019 Met Gala — and even hosted an afterparty together following fashion’s biggest night. In December 2019, Kendall was a guest during Harry’s hosting stint on The Late Late Show. According to Us Weekly, “Harry and Kendall are great friends and always have been.”

Nadine Leopold

From 2014 to 2015, the “Sign of the Times” singer and the Austrian model were photographed in Los Angeles on multiple occasions. It wasn’t until she appeared in the 2018 E! docuseries Model Squad that she spoke about her relationship with Harry, revealing that fans relentlessly attacked her during their courtship. Harry has yet to speak on their relationship.

Sara Sampaio

The Portuguese model was photographed hugging and kissing the “Kiwi” artist in June 2015. The pair reportedly spent a night together at a New York City hotel prior to the snapshots.

Georgia Fowler

The New Zealand native shared Snapchat videos of her and Harry playing Scrabble in October 2015, which sparked romance rumors. Speculation continued when Harry released his song “Kiwi” — which is also a nickname for New Zealanders.

The model denied the rumors on Australia’s The Morning Show. “[I] definitely didn’t have a baby,” she said. “That’s what the song’s all about, so I think it’s highly unlikely.”

Tess Ward

Harry and the food blogger were “casually seeing each other and [had] been on several dates” in 2017, but split in a matter of weeks, according to Us Weekly.

Camille Rowe

Harry and Camille only dated for a year, but the French model became a major inspiration. Harry’s close friend and collaborator Tom Hull told Rolling Stone in August 2019 that their breakup “had a big impact on him” and fueled his songwriting process for his second album.

Olivia Wilde

The “Ever Since New York” artist and the actress surprised fans when they went public with their relationship just two months after Olivia officially broke off her engagement. The new couple reportedly spent time together in London as Harry filmed his movie My Policeman and Olivia’s ex Jason shot season 2 of his series Ted Lasso.

The duo also sparked engagement rumors in April 2022 Instagram gossip account DeuxMoi reported that they were gearing up to tie the knot. Sadly, the report was the complete opposite of their future as they split seven months later.

Emily Ratajkowski

The “Watermelon Sugar” singer was spotted smooching model and actress Emily Ratajkowski on the streets of Tokyo in photos obtained by Daily Mail in March 2023.

Taylor Russell

Harry and the Canadian actress first sparked dating rumors in June 2023 when they were seen in public together in London.

The following month, a source exclusively told Life & Style that the pair was in the “early infatuation stage” of dating.

“He offered Taylor VIP seats to his upcoming concerts as well, so they can spend time together after the shows and get to know each other better. His crew likes her and thinks she’s really cool,” the insider said.

The source went on to note that Harry and Taylor’s relationship was “nothing serious at the moment but that doesn’t mean it couldn’t become serious down the road.”

The duo ​was spotted getting cozy together in August, though neither of them have publicly confirmed their ​relationship.