27 Mar, 2023


A Look At Harry Styles' Dating History: Kendall Jenner, Olivia Wilde, And More

By FactsWow Team

Caroline Flack

Over the years, he has dated women of all ages, including the late television presenter Caroline Flack and actor Olivia Wilde. It has always been a sensational relationship.

Media Credits: Yahoo Finance

Harry Styles & 'Old Flame' Ellis Calcuty

In London on Jan. 24, 2023, Harry Styles gathered with Ellis Calcutt, whom he reportedly dated when he was younger. Looks like the pair enjoyed a coffee and a walk together.

Media Credits: Hollywood Life

Olivia Wilde

Harry Styles visited Olivia Wilde's trailer during a filming session for 'Don't Worry, Darling' in November 2020. In August 2019, they were seen holding hands at a wedding.

Media Credits: E!Online

Emma Ostilly

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

Media Credits: Shutterstock

Emily Atack

During the 2012 presidential campaign, Emily Atack allegedly dated Harry, as seen here leaving The Palace Theatre in London.

Media Credits: Hello Magazine

Caggie Dunlop

A photo shows Caggie Dunlop at Fran Cutler's Halloween party at The Berners Tavern in 2019. Caggie Dunlop, shown here in 2012, is rumored to have dated Harry then.

Media Credits: Ok!Magazine

Taylor Swift

It dates between the end of 2012 and the beginning of 2013, when Harry Styles and Taylor Swift were photographed on this outing in Dec. 2012.

Media Credits: E!Online

Nicole Scherzinger

It was reportedly reported that Nicole Scherzinger briefly dated Harry in 2013 after she left Hakkasan restaurant in Mayfair.

Media Credits: Hollywood Life

Kendall Jenner

A picture of Harry Styles and Kendall Jenner leaving Craig's Restaurant in 2013 shows the couple dating on and off from 2013 to 2016.

Media Credits: Capital FM

Erin Foster

A 2014 romance was reportedly reported between Erin Foster and Harry, who appeared at the 2017 Baby2Baby Gala.

Media Credits: E!Online

Nadine Leopold

A 2014 report claims that Nadine Leopold dated Harry in 2014. Her appearance at the 2019 CFDA Fashion Awards proves this speculation.

Media Credits: The Mirror

Sara Sampaio

The actress Sara Sampaio is pictured here at the 2020 Vanity Fair Oscars party. She had a relationship with Harry reportedly in 2015.

Media Credits: CelebsFirst

Tess Ward

In 2017, Tess Ward was seen at the Australia House at The Strand in London, where she was reportedly rumored to have dated Harry.

Media Credits: HollywoodLife

Camille Rowe

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

Media Credits: Pinterest

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