Harry Styles is on top of the world right now.
After a “hiatus” from One Direction, Styles released his album Harry Styles, which has done extremely well, with tickets to his accompanying tour selling out in only 52 seconds.
While he is killing it with his career, who are the ladies that have defined Styles’ time in the spotlight?
Felicity Skinner 2009-2010
Skinner and Styles dated all the way back in 2009, right before Styles went on The X Factor. Apparently, the two just drifted apart after he started to become famous, but other sources say that Skinner is relieved that she gets to live her life out of the public eye and that is the reason things ended between the two. Either way, I am sure that they have both moved on since then.
Caroline Flack 2011
Styles’ relationship with Flack was his first (known) experience in cougar town. These two met when Styles was 17 and Flack was 31. At the time, Flack was a presenter on The X Factor, which is where she met Styles. In a PEOPLE article about the memoir Flack released in 2015 she comments on the relationship:
“I already knew that he had a crush on me, he’d made it pretty obvious. He’d said it in magazines and he’d said it to friends. Although it was just a bit of fun we decided it was best to keep it to ourselves…We were both single, we got on well and we had a laugh. It was only when it become public knowledge that things turned sour. At the beginning it was all very playful. He joked about being attracted to older women.”
When the relationship went public it was too much pressure for both of them so they ended it amicably.
Emma Ostilly 2012
Emma Ostilly is an American model.
This was more of a fling than a relationship, but the two met when they were both 18 and Ostilly was in One Direction’s video for “Gotta Be You” in New York.
Ostilly moved to New Zealand shortly after. When Styles was there with his band, the two were spotted on a date in Auckland, which ended with them kissing in the early hours of the morning outside of his hotel and then going inside together.
Whether this was a one-time fling or a casual relationship, it seemed fun while it lasted.
Taylor Swift 2012-2013
While this relationship seems like a bit of a trainwreck, we are still talking about it four years later, we got a couple of dope songs out of it so we can’t complain too much.
The two met at an award show in 2012 and on their second date they went for a stroll through Central Park and it became global news in five minutes. The next time they were spotted together was in the Caribbean which ended in the infamous picture of Swift alone on a boat as Styles was spotted in a hot tub with some older people.
About the relationship, Swift wrote “Out Of the Woods” and “Style.” In One Direction, Styles wrote “Perfect” and in his solo album, “Two Ghosts” and “Ever Since New York” are both rumored to be about Swift.
In a recent Rolling Stone article, Styles mentioned that the two aren’t on friendly terms but we hope they make up some day because how good would a Taylor Swift-Harry Styles collabo be?
Paige Reifler 2014
In 2014, the post-Taylor Swift era, model Paige Reifler told The Daily Mirror that she was seeing Styles after there were photos of the two in London.
According to a source, Styles was introducing Riefler as his girlfriend.
Things went south when one of Styles’ acquaintances posted, a picture of Riefler straddling and kissing Styles. When Riefler caught wind of the photo she commented “Take this down! Seriously not cool at all” and “this is no way to get back at me… Walter c’mon!”
While there was never any news of a conclusive end for these two, Styles has obviously moved on and the two are no longer a thing.
Kendall Jenner 2013-2016
In seemingly one of Styles’ longest lasting relationships, he has been linked with Jenner on and off for three years.
They were first spotted together in 2013 having dinner at Craig’s in LA.
The following January they were seen grabbing dinner and skiing and snowboarding together at Mammouth Mountain in California. This was the first time rumors of their relationship began because they were overtly acting like a couple.
The two weren’t spotted together for almost a year but then in December 2015, they were seen vacationing together in St. Barts. From paparazzi photos, it was obvious that the two were seeing each other because of pictures of Jenner lying on top of Styles and a pretty steamy makeout session. Things were even further confirmed when Jenner was targeted in an iCloud hack and pictures were released from the vacation with Jenner cuddling up to Styles, kissing his cheek and sitting on his lap.
In an interview with Entertainment Tonight, half-sister Khloe Kardashian said:
“They were hanging out together. Do I think they’re dating? Yes. 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,’” adding “but I mean, they were in St. Barts together hanging out, so to me that’s dating. I would call that dating.”
They were seen a couple months later shopping together and attending music agent Jack Azoff’s birthday party with their moms.
The last time the two were seen together was September 1, 2016.
These two were very cute together, so we are sad that it didn’t work out for them.
Tess Ward Present
Ward, a model turned food blogger and chef, has been rumored to be seeing Styles since early May. They were photographed together in Styles’ car and according to sources their relationship is the real deal and Styles has begun to introduce her to his friends.
We aren’t sure what the future holds for these two, but with the great career Harry Styles has got going we want him to have a great leading lady as well.