Olivia Wilde: Harry Styles’s latest rumored love interest is actress and director Olivia Wilde, who recently split from her fiancé of seven years, Jason Sudeikis. The two were seen holding hands at Harry Styles’s agent’s wedding on Jan. 3 and were photographed with luggage at his Los Angeles home the next day.
Caroline Flack: Harry Styles and Caroline Flack met when she was a presenter on The X Factor. Rumors started going around about Harry Styles having a crush on the British beauty around 2011, and shortly after, they both made waves when reports claimed they were dating, specifically due to their age gap at the time. Harry Styles was 17 and Caroline Flack was 31 at the time.
It began to go wrong when Harry Styles was pictured coming out of her house one morning. And once that was out, it was open season, after that anyone could say anything. In the street people started shouting at her ‘pedophile’ and ‘pervert.’
Emma Ostilly: Harry Styles was spotted kissing American model Emma Ostilly in New Zealand not too long after his split from Caroline Flack in 2011. She later appeared in the One Direction music video for “Gotta Be You”, which premiered in November of that year.
Emily Atack: Harry Styles was rumored to be dating actress Emily Atack back in 2012 but she didn’t confirm it until 2014. Although they have never been boyfriend and girlfriend, they had a short-lived thing that was just a bit of fun. Then they went off in our opposite directions.
Caggie Dunlop: In 2012, Harry Styles also reportedly dated actress Caggie Dunlop, who starred in the reality show, Made in Chelsea, for a brief time.
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.
Nicole Scherzinger: Harry Styles and lead singer of the Pussycat Dolls, Nicole Scherzinger, briefly hooked up in 2013. She was a judge on The X Factor when Harry Styles appeared on it in 2010.
Kendall Jenner: Harry Styles 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.
Erin Foster: Harry Styles 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 Hadid and Bella Hadid‘s (now ex) stepsister and her romance with Harry Styles seemed to be short-lived.
Nadine Leopold: Nadine Leopold was reportedly the first Victoria’s Secret model Harry Styles 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 Styles was seen kissing other Victoria’s Secret model, Sara Sampaio, in New York in 2015. The Portuguese pretty lady was also spotted leaving Harry Styles’s hotel the following day.
Georgia Fowler: Harry Styles 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 Styles 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.
Camilla Rowe: The third Victoria’s Secret supermodel Harry Styles 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 Styles’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.
Source: Hollywood Life