Harry Styles relationship timeline: From Taylor Swift to Olivia Wilde and Emily Ratajkowski


As one of our generation’s undisputed heartthrobs, Harry Styles’s relationship status is unsurprisingly a hot topic of conversation – especially following his public split from girlfriend Olivia Wilde and now his new reported romance with Taylor Russell.

It seems the Watermelon Sugar singer has recovered post-breakup and is ready to mingle once more. 

Harry was spotted cuddling up to Canadian actress Taylor, appearing to confirm their rumoured romance.

The pair were inseparable at the event on August 10, in pictures obtained by the Daily Mail.

His latest tryst comes months after he broke up with his Don’t Worry Darling director Olivia, who he dated for two years.

Before more rumours hit the airwaves, here’s a look back at all the leading ladies Harry’s been falling for over the years…

Caroline Flack

BRITAIN-ENTERTAINMENT-MUSIC-AWARD-BRITS
Harry and Caroline dated as he was rising to fame (Picture: Getty Images)

Caroline and Harry first crossed paths when he and other members of One Direction were on X Factor in 2011.

Their relationship, which lasted several months, was widely scrutinised owing to their 15 year age gap.

At the time, he was 17 and she was 32.

Emma Ostilly

Harry was then linked to model US Emma Ostilly in 2012, who he was snapped kissing on a night out in 2012, although he denied rumours they were dating.

Taylor Swift

Celebrity Sightings - Bauer-Griffin - 2012
Some of Taylor’s songs were thought to have been about the singer (Picture: GC Images)

Then, of course, there was Taylor Swift, who he was linked to for a few months between 2012 and 2013.

Taylor’s song Out Of The Woods and One Direction’s hit Perfect were apparently inspired by the relationship – although the pair never concretely confirmed these rumours.

Kendall Jenner

LOS ANGELES - DECEMBER 10: Harry Styles guest-hosts The Late Late Show with James Corden airing Tuesday, December 10, 2019, with guests Tracee Ellis Ross and Kendall Jenner. Pictured with: James Longman, Mike Schiff, Ben Winston. (Photo by Terence Patrick/CBS via Getty Images)
Harry and Kendall were on-again off-again (Picture: Getty Images)

Hazza’s also been linked to Kendall Jenner, with rumours that the pair were dating first starting up in late 2013.

They were snapped enjoying a string of dates in New York, LA and London, but their brief romance reportedly ended after just three months.

In December 2019, the rumours ramped up again when the pair flirted during an appearance on The Late Late Show.

Caitlyn Jenner confirmed the pair had dated in 2020 but didn’t go into specifics about when, or why they parted ways.

Camille Rowe 

Saint Laurent : Photocall - Paris Fashion Week - Womenswear Fall Winter 2023-2024
The star was linked with the model in 2018 (Picture: Getty Images)

Harry then dated Victoria’s Secret model Camille Rowe for just over a year, before they split in July 2018.

Fans were convinced his 2019 song Cherry features a voicemail message from Camille.

Olivia Wilde

London Celebrity Sightings - March 15, 2022
The couple split late last year (Picture: GC Images)

Fans were more than surprised when the former One Direction singer was spotted hand in hand with the actress and director Olivia Wilde, 39.

The pair were first seen at a friend’s wedding in January 2021.

Spending almost two years together, the famous faces put on a romantic display all over the world as Harry took his music on tour.

However, they called it quits in November of last year and a source told People: ‘He’s still touring and is now going abroad. She is focusing on her kids and her work in LA. It’s a very amicable decision.’

Emily Ratajkowski

NEW YORK, NY - SEPTEMBER 13: Emily Ratajkowski poses during New York Fashion Week: The Shows at Skylight at Moynihan Station on September 13, 2016 in New York City. (Photo by D Dipasupil/Getty Images)
The singer was snapped locking lips with the model (Picture: D Dipasupil/Getty Images)

Just four months after he split from Olivia, the singer was filmed sharing a sloppy snog with model and actress Emily.

The duo were locking lips on the busy streets of Tokyo.

Taylor Russell

In July, 29-year-old Taylor was spotted singing along in a VIP area at Harry’s Vienna gig, leading to suggestions that the pair might be linked.

2023 Film Independent Spirit Awards  - Arrivals
Lost In Space actress Taylor Russell appears to be Harry’s new love interest (Picture: FilmMagic)

They were also said to be spending time together in Vienna before parting ways and heading home.

More Trending

Then on August 10, Harry popped up at the press night for Taylor’s London theatre show The Effect. The two looked particularly cosy as they mingled with James Corden and, according to TMZ, Harry left the event alone and hopped into a car – with all of Taylor’s belongings.

He’s then said to have whizzed round to the stage door exit, at which Taylor jumped into the backseat with him and the pair drove off into the night.

If the rumours are true, the duo seem to be keeping things on the down low which isn’t a surprise given the high-profile nature of Harry’s past relationships, but we’re fully shipping them.

Got a story?

If you’ve got a celebrity story, video or pictures get in touch with the Metro.co.uk entertainment team by emailing us celebtips@metro.co.uk, calling 020 3615 2145 or by visiting our Submit Stuff page – we’d love to hear from you.


LONDON, ENGLAND - NOVEMBER 24: Erin Doherty and Sophie Melville attend the De Beers Jewellers London Flagship Store opening event on November 24, 2021 in London, England. (Photo by David M. Benett/Dave Benett/Getty Images for De Beers)

Adolescence star Erin Doherty splits from girlfriend Sophie Melville after seven years

Channel: Showbiz Showbiz March 25, 2025 By Stella Akinwumi
Harry Styles (L) grins as he sits next to James Corden outside cafe

Harry Styles flashes big smiles on pub day out with bestie James Corden

Channel: Showbiz Showbiz March 26, 2025 By Danni Scott