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Harry Styles’ Romantic History: Taylor Swift, Kendall Jenner & More

By:
Farrah Julin

From Taylor Swift to Kendall Jenner and more, look back at all the women who Harry Styles has dated.

1 of 17

Caroline Flack

Caroline Flack
Backgrid

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. From the late television presenter Caroline Flack to actress and director, Olivia Wilde, he’s dated women of all ages over the years and the situations have always made headlines.

Harry admitted to having a crush on Caroline when she was a presenter on ‘The X Factor’ during his time on the show. Dating rumors started shortly after in 2011 and the only thing Harry would say about the romance in interviews, was that they ‘got on really well’. Caroline later wrote about their connection in her book, Storm in a C Cup, which was released in 2015.

‘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 wrote about the ups and downs of their time together. ‘After that anyone could say anything. In the street people started shouting at me ‘pedophile’ and ‘pervert.’’

Caroline sadly died by suicide in Feb. 2020 and Harry was spotted honoring her by wearing a black ribbon at the 2020 BRIT Awards. 

January 4, 2021, 5:10PM
2 of 17

Untitled-1

Untitled-1
March 26, 2023, 11:27AM
3 of 17

Harry Styles and Olivia Wilde Exit Rubirosa Restaurant in NYC

Harry Styles and Olivia Wilde Exit Rubirosa Restaurant in NYC
MEGA

Harry Styles and Olivia Wilde Exit Rubirosa Restaurant in NYC Soho, NY. 18 Aug 2022 Pictured: Harry Styles, Olivia Wilde. Photo credit: MEGA TheMegaAgency.com +1 888 505 6342 (Mega Agency TagID: MEGA887653_004.jpg) [Photo via Mega Agency]

March 26, 2023, 11:26AM
4 of 17

Harry Styles & ‘Old Flame’ Ellis Calcuty

Harry Styles & ‘Old Flame’ Ellis Calcuty
MEGA

Harry Styles hung out with Ellis Calcuty in London on Jan. 24, 2023. It looks like the pair were happy to reconnect over coffee and a walk, after years apart. Harry was rumored to have dated Ellis when he was younger.

January 25, 2023, 10:36AM
5 of 17

Olivia Wilde

Olivia Wilde
CPR / Dsanchez / BACKGRID

Harry Styles is seen visiting Olivia Wilde’s trailer on the set of the film ‘Don’t Worry, Darling’ in Nov. 2020. They were spotted holding hands at a wedding two months later.

January 4, 2021, 5:10PM

More AboutHarry Styles

  • Harry Styles and Taylor Russell Pack on the PDA in London 10 Months After Olivia Wilde Split
  • Billy Porter Slams Harry Styles’ First Solo ‘Vogue’ Cover: ‘It Doesn’t Feel Good To Me’
  • Taylor Russell: 5 Things To Know About Harry Styles’ Rumored GF
6 of 17

Emma Ostilly

Emma Ostilly
PGagu68

Emma Ostilly, seen here at the 3rd annual amfAR Inspiration Gala New York at The New York Public Library in 2012, reportedly dated Harry in 2011.

January 4, 2021, 5:10PM
7 of 17

Emily Atack

Emily Atack
CLICK NEWS AND MEDIA / MEGA

Emily Atack, seen here leaving The Palace Theatre in London, reportedly dated Harry in 2012.

January 4, 2021, 5:10PM
8 of 17

Caggie Dunlop

Caggie Dunlop
MM / MEGA

Caggie Dunlop, seen here attending Fran Cutlers Halloween party at The Berners Tavern in 2019, reportedly dated Harry in 2012. 

 

 

January 4, 2021, 5:10PM
9 of 17

Taylor Swift

Taylor Swift
BACKGRID

Harry Styles and Taylor Swift, seen here during a Dec. 2012 outing, dated in the later part of 2012 until the first few days of 2013.

January 4, 2021, 5:10PM
10 of 17

Nicole Scherzinger

Nicole Scherzinger
Will / MEGA

Nicole Scherzinger, seen here leaving Hakkasan restaurant in Mayfair in 2014, reportedly briefly dated Harry in 2013.

January 4, 2021, 5:10PM
11 of 17

Kendall Jenner

Kendall Jenner
NGRE / AKM-GSI / BACKGRID

Harry Styles and Kendall Jenner, who reportedly dated on and off from 2013 until 2016, are seen leaving Craig’s Restaurant in 2013.

January 4, 2021, 5:10PM
12 of 17

Erin Foster

Erin Foster
AXELLE/BAUER-GRIFFIN / MEGA

Erin Foster, seen here at the 2017 Baby2Baby Gala, reportedly dated Harry in 2014.

January 4, 2021, 5:10PM
13 of 17

Nadine Leopold

Nadine Leopold
MEGA

Nadine Leopold, seen here at the CFDA Fashion Awards in 2019, reportedly dated Harry in 2014.

January 4, 2021, 5:10PM
14 of 17

Sara Sampaio

Sara Sampaio
Xavier Collin/Image Press Agency

Sara Sampaio, seen here at the 2020 Vanity Fair Oscars party, reportedly dated Harry in 2015.

January 4, 2021, 5:10PM
15 of 17

Georgia Fowler

Georgia Fowler
MEGA

Georgia Fowler, seen here during a 2019 outing, reportedly dated Harry in 2015.

January 4, 2021, 5:10PM
16 of 17

Tess Ward

Tess Ward
CAN/Capital Pictures / MEGA

Tess Ward, seen here at an event at the Australia House at The Strand in London in 2018, reportedly dated Harry in 2017.

January 4, 2021, 5:10PM
17 of 17

Camille Rowe

Camille Rowe
MEGA

Harry Styles and Camille Rowe, seen here after enjoying a dinner together in Hollywood in 2018, dated for a year.

January 4, 2021, 5:10PM
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