Harry Styles’ Romantic History: From Taylor Swift To Kendall Jenner, Holding Hands With Olivia Wilde & More

Harry Styles has had a number of relationships since he stepped into the international spotlight in 2010 and we’re taking a look back at them right here.

Harry Styles, 26, has been making girls swoon with his handsome looks, irresistible charm, and musical talent, ever since he stepped onto The X Factor stage for a televised audition to Stevie Wonder‘s “Isn’t She Lovely” in 2010, so it’s no wonder he’s led a steady romantic life over the years. Although the contestant-turned-superstar has many admirers from all over the world, only a few ladies have been lucky enough to be a part of his love life since he broke onto the music scene with his band One Direction and later started a successful solo career. From the late English television presenter, Caroline Flack, to his most recent rumored flame, actress and director, Olivia Wilde, we’re taking a look at all the gals who’ve been romantically linked to the British hunk.

Caroline Flack

Harry and Caroline met when she was a presenter on The X Factor. Rumors started going around about Harry having a crush on the British beauty around 2011, and shortly after, they both made waves when reports claimed they were dating. Harry was 17 and Caroline was 31 at the time.

Although neither confirmed nor denied a romance (Harry consistently said in interviews that they “just get on really well”), Caroline opened up about their connection years later in her autobiography, Storm in a C Cup, which was released in 2015. “I already knew that he had a crush on me, he’d made it pretty obvious,” she wrote in the book. “He’d said it in magazines and he’d said it to friends.”

“It began to go wrong when Harry was pictured coming out of my house one morning. And once that was out, it was open season,” she continued. “After that anyone could say anything. In the street people started shouting at me ‘pedophile’ and ‘pervert.’”

The two eventually split and moved on in their love lives, but sadly Caroline died by suicide at the age of 40 in Feb. 2020. Harry was spotted wearing a black ribbon as a “symbol of remembrance or mourning” to honor her at the 2020 BRIT Awards just a few days after her passing.

Emma Ostilly

Harry was spotted kissing American model Emma Ostilly in New Zealand not too long after his split from Caroline. She later appeared in the One Direction music video for “Gotta Be You”, which premiered in Nov. 2011.

Emily Atack

Harry was rumored to be dating actress Emily Atack back in 2012 but she didn’t confirm it until 2014. “We were never boyfriend and girlfriend…We had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions,” she told Reveal Magazine.

Caggie Dunlop

In 2012, Harry also reportedly dated actress Caggie Dunlop, who starred in the reality show, Made in Chelsea, for a brief time.

Taylor Swift

Who can forget Harry’s romance with fellow singer Taylor Swift? The two apparently met and clicked at the 2012 Kids Choice Awards before they were later spotted on numerous outings together (often hand-in-hand) during the latter part of 2012, and even shared a kiss in New York’s Times Square on New Year’s Eve during the first minute of 2013. They apparently split just a few days into the new year, however, but Taylor put the memories of the relationship to good use in songs on her highly successful album 1989, which was released in 2014.

Many of the tracks on the musical masterpiece are reportedly about Harry, including “Style”, “Out of the Woods”, and “I Wish You Would”. It was also rumored that Harry’s song “Two Ghosts” from his self-titled debut solo album, which was released in 2017, was about their relationship.

Nicole Scherzinger

The Sun reported that Harry and lead singer of the Pussycat Dolls, Nicole Scherzinger, hooked up in 2013. She was a judge on The X Factor when Harry appeared on it in 2010.

Kendall Jenner

Harry was first spotted having dinner in Los Angeles with Kendall Jenner in Nov. 2013. They were rumored to be dating until a split in Feb. 2014, but they seemed to be on again by 2015 and were seen canoodling on a yacht during the first days of 2016. Although they never confirmed their relationship, Kendall’s sister, Khloe Kardashian, admitted she thought they were “dating” in a 2016 interview with ET Online.

“Do I think they’re dating? Yes,” she told the outlet. “I don’t know if they’re like boyfriend-girlfriend. Nowadays I don’t know. People are weird with stuff. So, I don’t know their title.”

Erin Foster

Harry and writer Erin Foster were first spotted getting pumpkins at a pumpkin patch in 2014 and dating rumors started swirling right away. The blonde beauty was known for being Gigi and Bella Hadid‘s (now ex) stepsister and her romance with Harry seemed to be short-lived.

Nadine Leopold

Nadine Leopold was reportedly the first Victoria’s Secret supermodel Harry ever dated. They were first seen together in Nov. 2014 and followed that outing up with some frozen yogurt dates, but by March 2015, things seemed to be over.

Sara Sampaio

Harry was seen kissing other Victoria’s Secret model, Sara Sampaio, in New York in 2015. The Portuguese pretty lady was also spotted leaving Harry’s hotel the following day.

Georgia Fowler

Harry and model Georgia Fowler, who is from New Zealand, reportedly dated for a brief time in Oct. 2015. He was seen playing the board game Scrabble with her in a Snapchat video she posted around the same time.

Tess Ward

Harry reportedly had a brief relationship with chef and flood-blogger Tess Ward in the spring of 2017, but by June of the same year, things ended and she was soon seen back with her ex.

Camille Rowe

The third Victoria’s Secret supermodel Harry was romantically linked to was Camille Rowe in 2017 and 2018. Fans first started speculating they were dating when a voice that sounded like Harry’s could be heard in one of the French-American beauty’s Instagram stories. They were seen together on multiple occasions but split up after a year. One of Camille’s voicemails can be heard in Harry’s heartbreaking song “Cherry” from his 2019 sophomore album, Fine Line.

Olivia Wilde

Harry’s latest rumored love interest is actress and director Olivia, who recently split from her fiance of seven years, Jason Sudeikis. The two were seen holding hands at his agent’s wedding on Jan. 3 and were photographed with luggage at his Los Angeles home the next day. It’s not clear when the the stars first met, but Harry has been filming Don’t Worry, Darling, the latest movie directed by Olivia, over the past few weeks, so we can bet they’ve had time to get to know each other!