Alongside his music, Harry’s Styles sense of style has evolved over the years—and seemingly, both just keep getting better. After much anticipation, the singer released first solo album in 2017, featuring his first hit single “Sign of the Times.” The song is a sprawling five minutes and 41 seconds that touches upon musical styles of both Queen and David Bowie —a far cry from his teeny-bopper One Direction days. Then came the Stevie Nicks-approved Fine Line in 2019, which really solidified just how grown up the musician has become. He’s also embarked on a film career, having earned a role in Christopher Nolan’s 2017 film Dunkirk and Olivia Wilde’s upcoming period piece Don’t Worry Darling. And then there’s his fashion. Never one to stick to a traditional shirt and pants, the singer has come to be known for his affinity of high waisted trousers, pearl necklaces, and sparkly boots, preferably by Gucci and Saint Laurent. Here, a look back at his style evolution from teenage heartthrob to established fashion risk-taker.
2021
At the 2021 Grammys, Harry Styles wore not just one but three different feather boa looks—custom Gucci, of course.
2021
Harry Styles wears a bandanna (instead of a proper mask) while filming Don’t Worry Darling in 2021.
2020
Harry Styles performs at NPR’s Tiny Desk concert series in March 2020.
2020
Harry Styles visits SiriusXM Studios on March 02, 2020 in New York City.
2020
Harry Styles rehearsing for Today in the J.W. Anderson TikTok sweater.
2020
Harry Styles is seen performing at the Today show at the Rockefeller Plaza on February 26, 2020.
2020
Harry Styles attends The BRIT Awards 2020 in London, England.
2020
Harry Styles performs on stage during The BRIT Awards 2020 in London, England.
2020
Harry Styles posing with fans after leaving BBC Radio 2 on February 14, 2020 in London, England.
2019
Harry Styles spotted wearing his Fine Line t-shirt with pearls, as he leaves BBC Radio One on December 18, 2019 in London, England.
2019
Harry Styles wears a denim jumpsuit as he performs on stage during day one of Capital’s Jingle Bell Ball at London’s O2 Arena.
2019
Harry Styles seen wearing a sweater similar to Princess Diana’s sheep jumper on November 12, 2019 in New York City.
2019
Harry Styles attends the 2019 Met Gala Celebrating Camp: Notes on Fashion at Metropolitan Museum of Art on May 06, 2019 in New York City.
2019
Harry Styles stepping out in SoHo on March 29, 2019.
2018
Harry Styles attends the Casamigos Halloween Party on October 26, 2018 in Beverly Hills.
2018
Harry Styles performs onstage during Harry Styles: Live On Tour at Madison Square Garden on June 21, 2018.
2017
Harry Styles performs at the 2017 Victoria’s Secret Fashion Show in Shanghai, China.
2017
Harry Styles attends the 2017 iHeartRadio Music Festival in Las Vegas.
2017
Harry Styles attends “Dunkirk” Premiere at Ocine on July 16, 2017 in Dunkerque, France.
2017
Harry Styles attends the ‘Dunkirk’ World Premiere at Odeon Leicester Square on July 13, 2017 in London, England.
2017
Promoting his new album, Styles wears a red plaid suit out in London.
2017
Styles stays committed to Gucci in a logo sweatshirt while out in Paris in 2017.
2017
Styles performs on NBC’s “Today” at Rockefeller Plaza wearing a shocking pink suit.
2017
Harry Styles performs “Sign of the Times” in a Gucci suit on Saturday Night Live.
2016
Styles shows off his dramatic haircut, but keeps it classic in his fashion choices with a perfect fitting black suit and crisp white shirt.
2015
For the BBC Music Awards, Styles wore black and white vertical striped pants and a black shirt. Here he is on the red carpet with his bandmates from One Direction.
2015
Not ever afraid to take a risk on the red carpet, Styles wears a floral Gucci suit with wide-legged trousers.
2015
Styles greets his adoring fans in a navy spring coat and gray jeans on his way into BBC Radio 2.
2015
Fearlessly wearing a Gucci geometric print two-piece suit and black leather boots, Styles attended an event in London.
2015
Styles wears a bold Saint Laurent bomber jacket to perform One Direction’s latest single as part of Good Morning America’s summer concert series.
2014
Attending the Capital FM Summertime Ball with One Direction, Styles wears a chevron-printed shirt with a skinny scarf.
2014
Styles attends the Glam Rock Christmas Party in London in a revealing black shirt and long, striped trousers.
2014
Taking a major fashion risk on the red carpet, Styles wears a Lanvin striped suit and black boots.
2014
Performing with One Direction at the 2014 American Music Awards, Styles wears a gold embellished jacket and low-rise jeans.
2014
Styles, along with the other boys of One Direction, attend the Royal Variety Performance with the Royal family. Styles wears an animal print jacket over a black low-cut shirt.
2014
Styles goes full rock-and-roll at LAX in all black jeans and t-shirt, accessorized with a blue scarf, wide-brimmed hat, and sunglasses.
2014
At the launch for One Direction’s fragrance, Styles wears a oversized plaid shirt, unbuttoned in his usual manner, tight jeans, and a large hat.
2014
Seen out with friends (Hi, Ed Sheeran), Styles wears a Calvin Klein sweatshirt and a head scarf wrapped around his famous locks.
2013
For the 2013 British Fashion Awards, the London megastar shows up in a sheer black shirt, blazer, and a scarf.
2013
Styles wears a dark wool coat over an animal print shirt and black jeans at the Burberry Spring/Summer 2014 show.
2013
For the World Premiere of One Direction This is Us, Styles wears a heart print Burberry shirt under a black suit.
2013
Styles, showing off his tattoos in an unbuttoned shirt, and Miley Cyrus pose together backstage at the 2013 Teen Choice Awards.
2013
Seen in Miami Beach to film a One Direction music video, Styles steps out in unbuttoned plaid shirt and a tan hat.
2013
Styles gets buttoned up in a double-breasted suit and patterned shirt at a dinner in London.
2012
Harry Styles’ fashion for a 2012 taping of the Late Show With David Letterman with his band One Direction featured a monochromatic ensemble completed by leather moto boots.
2012
True to the trends, Styles wears a blazer with pushed up sleeves over a gray shirt at BBC Radio 1 Teen Awards.
2012
Styles goes casual with black jeans, a gray t-shirt and Converse while hanging out with Nick Grimshaw at the Shoreditch House in London.
2011
Styles is all smiles in a graphic tee and a sports coat greeting fans at BBC Radio in London.
2010
For an X Factor UK press conference, young Harry Styles arrives in classic black jeans and a gray button-down shirt.
Source: W Magazine
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