Harry Styles's Dating History, From Taylor Swift to Emily Ratajkowski

Way back in Style's "X Factor" days in late 2011 and early 2012, he was linked to the show's host, Caroline Flack. This was Styles's first high-profile romance, but things ended when the public caught wind of it. In January 2012, Styles reacted to their split on Twitter, writing, "She is one of the kindest, sweetest people I know. Please respect that." Following Flack's death in February 2020, Styles seemingly paid tribute to her by wearing a black remembrance ribbon to the BRIT Awards.

According to a report from the Daily Mail, Emma Ostilly, who starred in One Direction's "Gotta Be You" video, had some fun with Styles in late 2012 right around when he started talking to Taylor Swift. The fact that she lived in New Zealand at the time put a damper on what may have been a relationship, though, so it ended up just being a whirlwind fling.

Ah, the Swift days. While many believe this relationship was solely for the purpose of publicity, the fact remains that the two were linked for a period of a few months in late 2012 into early 2013. After "breaking up," Swift went on to write several songs supposedly about Styles ("Style" and "Out of the Woods," just to name a couple). In turn, Styles has also possibly written a few songs right back for her, like one of One Direction's last singles, "Perfect," and his solo song "Ever Since New York."

Styles and Kendall Jenner have been friends for several years and have had an on-again, off-again thing for most of it. Rumors of their relationship hit a new level when they were photographed getting very cozy on a yacht in the Caribbean during the holidays in late 2015. However, it seems like things were never too serious. They still get together as friends from time to time and even reconnected on "The Late Late Show With James Corden" in 2019.

Styles was rumored to be dating model Kara Rose Marshall after they were seen hanging out in New York with Styles's hairstylist back in 2013, per E News.

According to a 2013 report from Huffington Post, Rod Stewart himself let it slip in 2013 that Styles spent the night at his house when he was rumored to be dating Kimberly, his daughter.

In 2014, Styles was spotted in a few social media photos with model Paige Reifler before stepping out with her a couple times. However, things got messy when photos of the duo were posted by one of Styles's friends, prompting fan outrage, per the Daily Mail. After the scandal, Reifler and Styles weren't seen together again.

There's an ongoing joke that Styles has a winter girlfriend every year. In 2012, it was Swift; in 2013, it was Jenner; and in winter 2014, which rolled over into early 2015, it was Nadine Leopold. Styles and the model spent a lot of time together in LA before Styles and the rest of One Direction embarked on their last tour, but according to a report from Hollywood Life, Leopold and Styles split in early 2015.

Sara Sampaio and Styles briefly dated or hung out in 2015 not long after he and Leopold reportedly broke up, per E News. However, nothing else about this supposed encounter amounted to anything that expanded beyond a brief rumor.

Styles and model Georgia Fowler allegedly had a brief stint in 2015, according to a report from Stuff. The two apparently spent some time together away from the public eye in the Babington House hotel in Somerset, England, but nothing else really came from this. However, many fans speculate Styles's track "Kiwi" could be about Fowler, although she's denied the connection, per Grazia.

In 2017, Styles dated social media influencer and chef Tess Ward. Their new relationship was exclusively revealed in The Sun in the UK, something that Styles has never allowed in the past. The supposed relationship quickly fizzled, though.

One of Styles's most-publicized romances was with French Victoria's Secret model Camille Rowe. According to Teen Vogue, fans discovered the two were dating after they heard Styles's voice in Rowe's Instagram Story. Throughout their romance — which lasted from summer 2017 to July 2018 — the duo became extremely close, and Styles even introduced Rowe to his family, per Elle. However, the two eventually decided to part ways.

Styles addressed their split in his song "Cherry" from his 2019 album, "Fine Line". "I just miss your accent and your friends," he croons. The singer also includes an old voicemail from Rowe at the end of the track.

After working together on "Don't Worry Darling," which Styles and Wilde star in, the two sparked romance rumors when they were spotted holding hands at a friend's wedding in January 2021. A source told People, "They were affectionate around their friends, held hands, and looked very happy. They have dated for a few weeks."

Over the course of 2021, the duo would be seen together in various locations around the world, from the UK to Italy. In July 2021, the two were photographed kissing in Tuscany, further solidifying the dating rumors. However, nothing was officially confirmed until January 2022 when Wilde sat down with Vogue and discussed her relationship with Styles.

"It's obviously really tempting to correct a false narrative," she said. "But I think what you realize is that when you're really happy, it doesn't matter what strangers think about you. All that matters to you is what's real, and what you love, and who you love."

In May 2022, the two were spotted vacationing together in Italy. The photos came just weeks after Wilde was served legal papers stemming from her child-custody battle with her ex-fiancé, Jason Sudeikis, while on stage at CinemaCon, per Us Weekly.

The September 2022 release of "Don't Worry Darling" was, unfortunately, marred with controversy and speculation surrounding the couple as well. It all reached a fever pitch during the Venice premiere. The couple kept things super professional, forgoing walking the carpet together or sitting next to each other during the showing. (Although if they had sat together, they may have avoided all the speculation that Styles spit on his costar Chris Pine.)

In October of that year, Wilde and Styles were unwillingly dragged into more speculation when Wilde's former nanny claimed to the Daily Mail in an Oct. 17 article that Jason Sudeikis once threw himself in front of Wilde's car to stop her from visiting Styles with some of her reported special salad dressing in the final days of her tenure with the former couple. (Wilde and Sudeikis adamantly denied the rumors in a joint statement to POPSUGAR.)

The two officially split in November 2022. At the time, a source told People that they were "taking a break."

In late March, Styles and Emily Ratajkowski were spotted kissing in Japan as seen in a video and photos obtained by the Daily Mail. At this point, it's unclear whether the "Watermelon Sugar" singer and the model are dating or simply hanging out.