Like every former boybander in search of a solo career, Harry Styles had to create a new identity when One Direction split in 2016. But he didn’t just reinvent himself for the post-1D era. Styles, 29, has also been credited with reinventing manhood for a modern-day audience.
“Harry Styles is rewriting the rules of masculinity on his terms,” raved the women’s magazine Grazia in 2021. The New York Times heralded Styles last year for his “liberated” take on gender. That liberated take, though, hasn’t precluded him from reportedly having lots (and lots) of girlfriends.
According to reports this week, the model and actress Emily Ratajkowski is the latest in a string of famous and gorgeous women with whom Styles has been linked. There was the late Caroline Flack, who was presenting The Xtra Factor, the sister show of The X Factor, when Styles was a contestant in 2010 (she was 32 and he was 17). After that he went out with the comedian Emily Atack for a short time.
He also dated Kendall Jenner. His relationship with Taylor Swift was brief, but creatively fertile: her album 1989 is rumored to be shaped by their romance. There was a scattering of Victoria’s Secret models in between. Most recently, he was involved with the director Olivia Wilde (who cast him in the film Don’t Worry Darling) in the middle of a messy break-up with the father of her two children, the actor Jason Sudeikis.
There’s something quite retro about Styles’s romantic history, matching the dreamy Seventies influence in his music. His capacity for hooking up with the most impressive beauties of his era recalls the great shaggers of the 20th century — men like Mick Jagger, Warren Beatty and David Bowie, all of whom seemed to have had a cheerful kid-in-a-candy store attitude to sexual possibilities afforded by celebrity.
But serial dating can look tawdry rather than glamorous in the 21st century. Think of the general shudder greeting the actor Leonardo DiCaprio’s endless procession of young girlfriends, none of whom seem to last beyond their 25th birthday.
The New York Times heralded Styles last year for his “liberated” take on gender.
So how does Styles do it? He has always rejected the playboy label, and his version of maturity is different from the laddish one espoused by previous teen idols turned adult stars. See Robbie Williams, obliterating his Take That pinup status in 1995 by partying with Oasis at Glastonbury. Or Justin Timberlake, making vulgar comments about his ex Britney Spears in 2002 to kill off his nice-guy ’N Sync image.
No such boorishness for Styles. He is, instead, the gold standard of modern sensitivity. He wore a dress on the cover of Vogue, and a sheer blouse and pearl earring to the Met Gala in New York. In the film My Policeman, he played one half of a tender gay romance, and he’s lent his support to causes including Black Lives Matter and LGBT rights. At one concert, he supported a fan in coming out to her mother, leading the whole audience in a chant of: “Tina, she’s gay.”
This image has helped to make him staggeringly successful: his 2022 album Harry’s House broke streaming records, won best album at the Brits and the Grammys and spawned a 15-night residency at New York’s Madison Square Garden. Coupled with his delicate handsomeness, this may explain the queue of girlfriends.
Like his ex Swift, Styles has pointed out that he doesn’t actually date more than the average person his age — he just attracts more attention when he does. In the case of Ratajkowski, one photograph of the two kissing in the street in Tokyo has been worldwide news for days.
His capacity for hooking up with the most impressive beauties of his era recalls the great shaggers of the 20th century.
In response, Styles maintains the gentlemanly habit of rarely discussing his love life. It’s not far off the old music industry wisdom that heartthrobs should avoid relationships to keep themselves notionally available to their fans. But it also protects him. Having been famous since he was 16, Styles has had to learn to draw a line between his public and private selves to survive. And it protects the woman he’s with from jealous fans, who perceive any girlfriend as a rival to be attacked. A corner of his fandom can be “crazy” and “mean”, he has said.
Styles’s respect for his partners is in line with contemporary manners. Timberlake initially gained credibility for trashing Spears but by 2021, at the peak of #FreeBritney outrage, upset fans pushed him into a groveling apology nearly 20 years on. Chivalry is back in fashion.
Styles also gets points for his apparent fearlessness around women who are impressive on their own terms. While the age gap with Flack raised eyebrows at the time, he’s subsequently been linked to multiple older, accomplished women.
Unlike a lot of famous men, he seems happy to be with an equal — or even, in the case of Swift, her muse. He also keeps things amicable post-break-up and has made friendly appearances with Swift and Jenner.
Beatty is also known for keeping his exes close. “What happens is fame gives you access, so you’re lucky enough to be exposed to these very admirable women,” the actor said in 2016. “Not just physically beautiful, but great people and talented and intelligent people.”
Harry Styles hasn’t reinvented masculinity but maybe he’s rediscovered the trick that separates a great lover from a playboy: he actually seems to like women, as well as wanting to sleep with them.
Sarah Ditum is a London-based journalist
