Harry Styles' Unconventional Evolution From Boy Bander to Bona Fide Pop Superstar

Here's a look at how the 26-year-old artist paved his own way in music, film and fashion.

At 26 years old, Harry Styles is a bona fide pop superstar. The British artist may have started his musical career as one-fifth of the mega boy band One Direction, but with his solo career, he has cemented himself in music history with his unconventional sound, look and public persona.

Recently making history as Vogue first-ever solo male cover star, and better yet donning a lace-adorned Gucci gown, ET is taking a look at how Styles has paved his own unique way in both the entertainment and fashion industries.

Breaking the Boy Band Mold

Musically, after One Direction disbanded in 2016, Styles' solo debut single, "Sign of the Times," was a breath of fresh air for the singer, who took a somewhat unexpected direction with his sound. The melancholic song peaked at No. 4 on the U.S. Billboard Hot 100 and was named "Song of the Year" by Rolling Stone in 2017. His '70s soft-rock vibe self-titled debut album also topped the charts in 14 countries.

His second album, Fine Line (2019), debuted at No.1 on the U.S. Billboard 200, breaking the record as the biggest sales debut from an English male artist in the U.S. While Styles released four singles from the LP, it was "Adore You" and "Watermelon Sugar" (and their accompanying music videos) that enamored fans and critics with their quirky and cheeky nuances. The latter also became Styles' first No. 1 single on the Billboard Hot 100 chart.

Add to that two successful headlining tours and playing for 36,000 people at Madison Square Garden in New York and major arenas all over the world. He also made quite an impressive acting debut in Christopher Nolan’s 2017 Oscar-nominated war movie, Dunkirk. The famed director even admitted to being unaware of Styles' fame and cast him out of more than a hundred actors "because he fit the part wonderfully and truly earned a seat at the table."

Styles' unmeasurable talent also extends to exceptionally guest hosting The Late Late Show With James Corden on multiple occasions.

Modern-Day Icon of Genderless Fashion

During his time with One Direction, Styles' fashion evolved from typical teen boy bander, rocking skinny jeans, T-shirts and hoodies, to experimenting with printed suits, glitter-heeled boots and neckties. As he found his own style as a solo artist, he began breaking out of his shell, opting for a slew of genderless fashion, including wearing nail polish, harnesses, flamboyant suits and jewelry.

"I used to wear all black all of the time. But I was realizing [dressing up] was a part of the show, if you will. Especially when performing," he said in a 2019 Dazed interview. "So, I think [for] the people I have always admired and looked up to in music, clothes have always been a big part of the thing. Like Bowie, Elvis Presley. It's always been part of the thing."

Not one to shy away from ruffles and frills, the performer went on to effortlessly fuse rocker fashions of the ’60s and ’70s, donning a "New Romantic-inspired take on rock ’n roll dressing," as designer Harris Reed, who collaborated with Styles on the looks for his tour, told Miss Vogue.

A big fashion moment for the "Sweet Creature" crooner was when he stepped out at the 2019 Met Gala wearing a sheer black blouse with a pussy bow and a pearl earring -- becoming a full-fledged fashion icon. "It's about enjoyment and about fun," Styles, who was a co-chair of the event, told Vogue of the Camp theme and his style choices. "No judgment, having fun with clothes. I think fashion is supposed to be fun. And I think it's a good time for that right now with people being who they are."

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Embracing his sexual ambiguity -- a la Mick Jagger, Queen and Bowie -- for Styles, fashion is not a question of "what women wear. What men wear."

"If I see a nice shirt and get told, 'But it's for ladies.' I think: 'Okaaaay? Doesn't make me want to wear it less though,'" he explained in a 2019 interview with The Guardian. "I think the moment you feel more comfortable with yourself, it all becomes a lot easier."

“A part of it was having, like, a big moment of self-reflection. And self-acceptance," Styles noted. "I think it’s a very free, and freeing, time. I think people are asking 'Why not?' a lot more. Which excites me. It's not just clothes where lines have been blurred, it’s going across so many things. I think you can relate it to music, and how genres are blurring."

Offstage, Styles' look is just as impressive. His streetwear is also a mix of feminine pieces, which have included collared sweaters with lace detail, funky sunglasses and a pearl necklace, which he's worn on multiple occasions.

"Just going on stage in a nuts suit with a bunch of sequins makes you feel good, and then you want to play," Styles told Dazed, noting of his offstage looks and how he's also embraced flared pants. "I had never really done flares before. And it was really fun. I just kind of started wearing more and more of it, and at the same time just becoming a lot more comfortable in myself."

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His style choices have even given him the seal of approval from Vogue, who has called him the "icon of modern masculinity -- a role he’s assumed with admirable nonchalance." The fashion magazine went one step further when they chose him as the 2020 December cover star, making him the first-ever solo male artist to cover Vogue.

Of greater note than the history-making cover itself was what Styles dons on it, a stunning, lace-adorned Gucci gown. Dresses, Styles said, have been a favorite of his since childhood when he got in costume for a play.

"As a kid I definitely liked fancy dress," the singer noted in the accompanying interview. "I was really young, and I wore tights for [the play]. I remember it was crazy to me that I was wearing a pair of tights. And that was maybe where it all kicked off!"

Styles also called the popularity gender-nonconforming style "really exciting," adding that "all of these lines are just kind of crumbling away."

New Take on Masculinity and His Most Authentic Self

Styles isn't one for labels and doesn't care for talk about his sexuality or the ambiguity of it.

"It’s: 'Who cares?' Does that make sense? It’s just: 'Who cares?'" he told The Guardian at the end of last year when questioned about his sexuality. "Am I sprinkling in nuggets of sexual ambiguity to try and be more interesting? No. In terms of how I wanna dress, and what the album sleeve’s gonna be, I tend to make decisions in terms of collaborators I want to work with."

"I want things to look a certain way. Not because it makes me look gay, or it makes me look straight, or it makes me look bisexual, but because I think it looks cool," he stated. "And more than that, I dunno, I just think sexuality’s something that’s fun. Honestly? I can’t say I’ve given it any more thought than that.”

Being his most authentic self, he's also shied away from controversial headlines or major relationships that raise his profile. Not since his 2012 short-lived relationship with Taylor Swift and private time with Kendall Jenner has the British rocker been attached to a high-profile public relationship.

He has, however, been vocal about the close friendships he's maintained, and how open and honest he and his mates are with each other.

"I feel pretty lucky to have a group of friends who are guys who would talk about their emotions and be really open," he shared with Rolling Stone. "My friend's dad said to me, 'You guys are so much better at it than we are. I never had friends I could really talk to. It's good that you guys have each other because you talk about real sh*t. We just didn't.'"

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But, at the same time, he knows how to bring it with the gossip and just have fun. He is, after all, an entertainer. Styles knew all too well that media and fans would be intrigued to see what went on between him and Jenner when she was the special guest during his hosting duties on the Late Late Show at the end of last year.

While the two never confirmed their rumored romance, during a game of "Spill Your Guts or Fill Your Guts," the model outright asked him, "Which songs from your last album were about me?"

He initially began to reply, saying, "So I'd say track... ummm," before slicing into some cod sperm and taking a bite to avoid answering the question.

An Ally for the LGBTQ Community and Social Justice

In 2020, being a musical genius and fashion icon aren't the only requisites for being a bona fide superstar. Styles is also known for unapologetically speaking out for the LGBTQ community, Black Lives Matter and other social issues.

"I want to make people feel comfortable being whatever they want to be," he explained in a Rolling Stone interview. "Maybe at a show you can have a moment of knowing that you're not alone. I'm aware that as a white male, I don't go through the same things as a lot of the people that come to the shows. I can't claim that I know what it's like, because I don't. So I'm not trying to say, 'I understand what it's like.' I'm just trying to make people feel included and seen."

During a 2018 concert in San Jose, California, Styles even helped a fan come out to her mother after she made a sign that said she was going to come out to her family because of him.

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Additionally while on tour, he waved the Pride flag and sold rainbow T-shirts with the phrase “Treat People With Kindness" that benefited the LGBTQ organization GLSEN.

"It’s not about me trying to champion the cause, because I’m not the person to do that,” he stated. “It’s just about not ignoring it, I guess. I was a little nervous to do that because the last thing I wanted was for it to feel like I was saying, ‘Look at me! I’m the good guy!’ I didn’t want anyone who was really involved in the movement to think, ‘What the f**k do you know?’ But then when I did it, I realized people got it. Everyone in that room is on the same page and everyone knows what I stand for. I’m not saying I understand how it feels. I’m just trying to say, ‘I see you.'"

He's supported the #HeForShe campaign (a solidarity movement for gender equality), raised awareness for Stonewall Gay Rights Charity and participated in events with the Lalela Project (a Cape Town-based organization that helps teach arts education to at-risk youth).

He's also all about equality, and some would consider him a feminist.

“I think ultimately feminism is thinking that men and women should be equal, right? People think that if you say ‘I’m a feminist,’ it means you think men should burn in hell and women should trample on their necks. No, you think women should be equal," he described to Rolling Stone. "That doesn’t feel like a crazy thing to me. I grew up with my mum and my sister -- when you grow up around women, your female influence is just bigger. Of course men and women should be equal. I don’t want a lot of credit for being a feminist. It’s pretty simple. I think the ideals of feminism are pretty straightforward."

And, most recently in May, following the murder of George Floyd, Styles took to his Instagram to pen a passionate statement on the Black Lives Matter protests, expressing his solidarity for all those marching.

He also took to the streets in protest, standing with other people speaking out against racial injustice and police brutality. The singer also donated money to help post bail for arrested organizers.

True to His Roots

Styles has managed to grow up in the public eye without getting a negative rep or going down a bad road of drugs and scandal. And unlike some musicians who've talked ill about the boy bands that made them famous, Styles has never diminished his time with One Direction.

"I know it's the thing that always happens. When somebody gets out of a band, they go, 'That wasn't me. I was held back,'" he's noted to Rolling Stone. "But it was me. And I don't feel like I was held back at all. It was so much fun. If I didn't enjoy it, I wouldn't have done it. It's not like I was tied to a radiator."

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In July, to celebrate the 10-year anniversary of 1D, Styles penned a heartfelt message about his wonderful time in the band. "I’ve been struggling to put into words how grateful I am for everything that’s happened over the last ten years. I’ve seen things and places that I’d only ever dreamt of when I was growing up," he wrote. "I’ve had the pleasure of meeting and working with some of the most incredible people, and gained friendships that I know I will treasure for the rest of my life. None of this would be possible without the support you’ve given along the way."

Writing that he can't believe it's been 10 years since the band was formed, he thanked everyone for their support before saluting his former groupmates Niall Horan, Louis Tomlinson, Liam Payne and Zayn Malik.

"And finally.. to the boys, I love you so much, and I couldn’t be prouder of everything we achieved together," he added. "Here’s to ten. H."

A natural class act, Styles is the superstar the world needs and wants.

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