Love him or hate him, Harry Styles is one of the most sought-after musicians in the entire world. Boasting over 28 million Twitter and 18 million Instagram followers on his personal accounts alone, this One Direction heartthrob has truly had one successful ride since his X Factor days!

Here are 7 beautiful girls Harry Styles has dated (with pictures).


Harry Styles and Abigail Crawshaw go way, way back (pictured below is the pair from 2007). The two began dating at the tender age of 12, and managed to keep in contact throughout One Direction’s rise to international fame. Fast forward to 2015, and it’s clear that the two are still on good terms having met up again backstage in Newcastle on One Direction’s On The Road Again Tour.

Sources say that Abigail was in fact Harry’s first-ever girlfriend, which is believable given that they were only 12 at the time! These days, Abigail remains out of the spotlight and enjoys traveling, emojis, and The Weekend.


Harry and Felicity Skinner began dating back in the summer of 2009 when they were both 15-years-old. According to The People, a British tabloid magazine, Felicity, now 22, claims to have bee Harry’s “first love” and that their relationship lasted “just under one year”. She also notes that the two met through a mutual friend, “Liv”, and clicked right away.

The pair lost contact as they began to see their lives drift in opposite directions with Harry soaring to fame after his X Factor run and Felicity staying at home to continue her studies. Felicity admits that they don’t talk anymore, with distance playing a role in their split. She does note that the two left on good terms, with Harry having been very romantic.


Coined a “very inappropriate relationship” for their 14 year age difference by media outlets, Directioners, and the general public, Harry Styles and Caroline Flack began dating back in 2011 after meeting on The X Factor. Caroline, 31 at the time, and Harry 17, saw nothing wrong with their age difference (the age of consent in the U.K. is 16).

Harry is known for his interest in the cougar department, and sees no wrong with it unless the woman is older than his mum. The pair broke up shortly before Harry’s 18th birthday and tweeted that their breakup was a mutual decision.


Rumor has it that American model and star of One Direction’s “Gotta Be You music video, Emma Ostilly, was at the heart of Harry’s breakup with Taylor Swift following a steamy photo taken in April 2012 of the two kissing outside her Auckland home. The photo, taken in the early hours of the morning, created so much outrage among Directioners that Emma was forced to delete her Twitter account for the time being.


Harry and Taylor Swift’s short-lived relationship of 2012/2013 is arguably Harry’s most publicized and talked about relationship to date. Granted, Taylor Swift is the biggest pop star since Michael Jackson. Regardless, their messy fallout was expressed in numerous songs such as “Out of the Woods” on Taylor’s 1989 album as well as “End of the Day” on One Direction’s Made In The AM album, which both reference their near-death snowmobile accident.

In a 2015 Grammy interview, Taylor recalls feeling anxiety while dating Harry, pointing out that their entire relationship was fragile, always feeling that a road block lie ahead. Despite their split in January 2013, WE WILL NEVER FORGET those matching paper airplane necklaces!


There’s no denying that this racy pic is of Harry Styles and Paige Reifler. I mean c’mon, Harry’s forearm tattoo and infamous brown boots are on full display!

This short-lived relationship is unconfirmed, but the two are believed to have linked up in NYC during One Direction’s “Take Me Home” summer tour.

Sources claim that Paige’s (former) friends Walter Martinez, Stephen Orso, and Alec Orso blackmailed her by trying to sell the picture below to TMZ, but decided to post it to Instagram instead. One Direction fans quickly caught on to the picture, which prompted a spew of hateful comments towards Paige and further speculation of a possible relationship between the two.

Judging from Paige’s response pictured below, do you think she was REALLY mad about the picture being posted? Or does it appear she is hungry for fame?


Social media lost its mind when Harry Styles and Kendall Jenner were pictured ringing in the new year hooking up on a yacht in St. Barths. What’s even better? Kendall’s mother, Kris Jenner, and Harry’s mother, Anne Cox, were present on the getaway!

The pair are believed to have started dating in 2013 and are reported to still be linked despite their busy careers thanks to numerous mutual friends.