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

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

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Caroline Flack

Caroline Flack — 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.

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Harry Styles and Olivia Wilde Exit Rubirosa Restaurant in NYC

Harry Styles and Olivia Wilde Exit Rubirosa Restaurant in NYC — 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]

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Harry Styles & ‘Old Flame’ Ellis Calcuty

Harry Styles & ‘Old Flame’ Ellis Calcuty — 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.

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Olivia Wilde

Olivia Wilde — 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.

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Emma Ostilly

Emma Ostilly — 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.

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Emily Atack

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

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Caggie Dunlop

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

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Taylor Swift

Taylor Swift — 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.

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Nicole Scherzinger

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

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Kendall Jenner

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

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Erin Foster

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

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Nadine Leopold

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

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Sara Sampaio

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

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Georgia Fowler

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

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Tess Ward

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

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Camille Rowe

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

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