The "Adore You" singer, 26, has sparked dating rumors with actress Olivia Wilde, 36, after the two were photographed holding hands at a wedding in Montecito, California, over the weekend. ET has learned that the two attended the wedding of Styles' manager, Jeffrey Azoff, who works in Artist Relations at Apple Music.
"To me, he's very modern," Wilde -- who is directing Styles in her upcoming psychological thriller, Don't Worry Darling -- told Vogue last month, for the former One Direction star's history-making cover. "I hope that this brand of confidence as a male that Harry has, truly devoid of any traces of toxic masculinity, is indicative of his generation and therefore the future of the world."
"I think he is in many ways championing that, spearheading that," she added. "It's pretty powerful and kind of extraordinary to see someone in his position redefining what it can mean to be a man with confidence."
Of course, this isn't the first time Styles has made headlines for being romantically linked to someone in the public eye. ET's taking a look back at the singer's dating history, including his highly publicized romances with stars like Kendall Jenner and Taylor Swift.
Rumors that Styles was connected to the model began swirling in early 2019, but they were quickly shut down when Mizuhara claimed via Twitter that she had never even met Styles.
"It has been reported that I and Harry Styles are dating, but I have never been dating him and I have never met him," she tweeted at the time. "Everyone, the world is full of fake news. Don't let the media dance!"
One month later, however, Mizuhara was spotted partying at Styles' 25th birthday bash in Tokyo in a video that made the rounds on social media. While it appeared they knew each other, further speculation of a romance seemed to fizzle out.
Styles' relationship with the French model seemed to be his longest to date. They broke up in July 2018, just over a year of dating.
In a 2019 interview with Rolling Stone, one of Styles' best friends, Tom Hull, told the magazine that the singer took his breakup from Rowe hard. And although Styles didn't mention Rowe by name in his accompanying interview, he said that his music is the only arena in which he discusses his personal life.
"For me, it doesn't mean I'll sit down and be like, 'This is what I have for dinner, and this is where I eat every day, and this is what I do before I go to bed,'" Styles said at the time. "But I will tell you that I can be really pathetic when I'm jealous. Feeling happier than I've ever been, sadder than I've ever been, feeling sorry for myself, being mad at myself, being petty and pitiful -- it feels really different to share that."
2017: Tess Ward
In the spring of 2017, romance rumors began swirling that Styles was dating the chef and food blogger. Ward reportedly ended things in June, however, to get back together with her ex-boyfriend.
In an October 2017 interview with Nick Grimshaw on The Radio 1 Breakfast Show, Styles admitted that he used to research dates. "Then I said I'm not going to do that anymore," he said. "It's impossible to go in without a perception of someone and you've never met them and I started feeling like that was wrong and weird."
"I feel like with all of the stuff -- how people date now, with all online stuff -- I feel like you can do that [Google] with anyone," he added. "Really, if you're looking at someone's profile before seeing them it's kinda the same."
2016: Pandora Lennard
According to a report from U.K.'s The Sun, Lennard was spotted leaving Styles' London home in early January 2016, after spending the night. The sighting came just a few weeks after Styles' romantic getaway to St. Barts with Kendall Jenner.
"Do I think they're dating? Yes," she said. "I don't know if they're like boyfriend-girlfriend. Nowadays I don't know. People are weird with stuff. So, I don't know their title."
"They were in St. Barts together hanging out. So to me that's dating," she continued. "I would call that dating. [But] I don't know what they are. You know, you have to have 'the talk' [and] I don't know if they've had that talk yet."
2015: Georgia Fowler
Styles and Fowler were rumored to be seeing each other briefly in 2015, after the New Zealand model posted a video to her Snapchat of the two playing Scrabble.
2014-2015: Nadine Leopold
While Styles and the Australian model were spotted on several outings together, their rumored romance was short-lived. It appears the two went their separate ways in March 2015, after approximately four months of dating.
2012-2013: Taylor Swift
From October 2012 to January 2013, Styles found himself in a whirlwind romance with the pop star, with dates spanning from a day out at the Central Park Zoo in New York City to a romantic getaway to the British Virgin Islands.
"Certain things don't work out," Styles later said of their relationship, in a 2017 interview with Rolling Stone. "There’s a lot of things that can be right, and it's still wrong."
In that same interview, Styles was asked whether he thought "Out of the Woods" and "Style" -- songs from Swift's 1989 album -- were written about him.
"I mean, I don't know if they're about me or not…but the issue is, she's so good, they're bloody everywhere," he responded. "I write from my experiences; everyone does that. I'm lucky if everything [we went through together] helped create those songs. That's what hits your heart."
"In writing songs about stuff like that, I like tipping a hat to the time together. You're celebrating the fact it was powerful and made you feel something, rather than, 'This didn't work out, and that's bad,'" he added. "And if you run into that person, maybe it's awkward, maybe you have to get drunk, but you shared something. Meeting someone new, sharing those experiences, it's the best s**t ever. So thank you."
2012: Emily Atack
Styles and the British actress reportedly dated quietly in 2012. The Inbetweeners star confirmed they were an item two years later in an interview with Reveal magazine.
“We had a short-lived thing that was just a bit of fun," Atack said. "Then we went off in our opposite directions."
2011: Caroline Flack
Styles briefly dated the TV host in 2011 shortly after he gained fame with One Direction on The X Factor. The relationship was seen as controversial at the time, due to their 14-year age gap.
"I still feel 18 and probably act that way half the time," Flack explained in her Storm in a C Cup autobiography. "Although it was just a bit of fun we decided it was best to keep it to ourselves as we were both working for Simon Cowell."
"We were both single, we got on well and we had a laugh," she continued. "It was only when it became public knowledge that things turned sour."
Flack died last February at the age of 40, and Styles appeared to pay tribute to her that month while attending the Brit Awards in London, England. He wore a black ribbon -- traditionally a symbol of remembrance or mourning -- on his lapel, seemingly in memory of his ex.