From Graphic Tees to Gucci: Harry Styles’ Fashion Transformation

Photo from rollingstones.com

From dressing like a frat boy in his early One Direction days to wearing the most notable designers at places like the Met Gala, it’s pretty obvious Harry Styles’ sense of fashion has taken a complete 180. Whether he was sporting flannels and flashy sneakers or turtlenecks and nail polish, Harry has certainly amped up his fashion game, and the world cannot get enough of it. With clothes that seem to reflect the choices he’s made in his music career, Harry has made it clear he is not one of the men in Hollywood who wears a navy blue suit instead of a black one to an event and calls it a “fashion statement”.

VALLEY is taking an in-depth, year-by-year look at the “Watermelon Sugar” singer’s style evolution starting from his earliest days in show business to his most recent musical endeavors.

Photo from vogue.com

2010: “The X-Factor” Days

When Harry Styles first arrived on the music scene, he stole the hearts of millions everywhere on “The X Factor” with his mega-watt smile, curly hair and adorable dimples. Harry donned a grey cardigan, white t-shirt, black skinny jeans and printed scarf for his first “X Factor” audition–a pretty fashion-forward choice for that time in fashion. Throughout the rest of his time on the show with One Direction, Harry wore a lot of early 2010s typical outfits, such as button-ups, plain t-shirts, blazers and scarves, usually color coordinating or matching with the four other boys of the group.

Harry’s initial X Factor audition, singing “Isn’t She Lovely” and wearing a wrist full of bracelets. 10 years later, this is a fashion mishap but was quite a look for 2010.
Photo from thethings.com
Harry with Louis, Zayn, Niall, Liam, and Simon Cowell after a performance on “The X Factor”, donning khakis, a white t-shirt and blue button-up shirt, a very typical male outfit of the early 2010s.
Photo from pinterest.com
After another “X Factor” performance with the rest of the boys of 1D, wearing matching gray ensembles and red ribbons for National AIDS Day. The color coordination was a recurring theme in the early days of 1D, and this look was no exception.
Photo from eonline.com

2011: The Rise of One Direction

If you were a girl in 2011, you probably had One Direction Infection, just like the rest of the world’s adolescent female population at the time. It was impossible to go anywhere without hearing “What Makes You Beautiful” or seeing their faces on the front of every magazine. Everyone had a favorite member of the band and was obsessed with learning everything about them. Each of the boys had a distinct personality and identity in the group, so as to differentiate themselves from one another. Harry was considered the flirt of the group, and his style began to reflect that. Whether he was sporting plain t-shirts and a simple necklace or suits and ties, Harry’s clothes were classic and preppy.

Was it really 2011 if Harry Styles didn’t wear a plain white V-neck with a chain and bracelets? Absolutely not.
Photo from pinterest.com
As One Direction garnered popularity, the boys’ fashion game was expected to step up. Very true to the times, Harry sported a bow tie with his blazer for an award show very early in 1D’s career. The preppy look really suited his flirty persona, and the rolled sleeves added a certain je ne sais quoi.
Photo from fashion-north.com
Ah, the classic open-blazer-over-the-graphic-tee look. This was so quintessentially 2011 Harry that there is absolutely no way there could be a visual gallery of Harry Styles without at least one of these bad boys. Whether the shirt under the blazer had a print or was a plain t-shirt, Harry wore this look so many times early in One Direction’s career that it was hard to narrow down just one of these looks.
Photo from pinterest.com

2012: The Height of One Direction Infection

By 2012, One Direction had completely taken over the music scene. Their debut studio album “Up All Night” was a commercial and international success, and their tour of the same name was skyrocketing in ticket sales. The boys of 1D had books, posters, dolls, cardboard cutouts and, most notably, the most popular genre of Wattpad fanfiction. 2012 was the year

One Direction performed at the closing ceremony of the Olympics, the band had won three MTV Video Music Awards, rumors of Harry dating Taylor Swift began to circulate and, most importantly, when Harry began to grow his hair out. Harry, while still rocking his signature t-shirts, began to substitute blazers for beanies and flannels, shifting his style from preppy to a little more hipster.

In January of 2012, Harry was still deep in his preppy phase. This look from the “Up All Night” tour was classic Harry, from the t-shirt to the navy blue blazer, to the little “H” embroidered on it.
Photo from cosmopolitan.com
This was around the time Harry started to shift in his fashion sense. The brown jacket and color coordinating flannel were a little scruffier than Harry’s typical looks for the time, but were a good transitional look and eased fans into a new era of Harry’s personal style.
Photo from pinterest.com
This was the beginning of a very beautiful friendship: Harry Styles and beanies. This outfit was early in Harry’s relationship with Taylor Swift, and very early in his days of grunge-esque style. The converse, t-shirt with the little pocket, and nearly empty wrist (spare the watch and singular bracelet) were simple yet effective.
Photo from usmagazine.com

2013: “Midnight Memories,” “This Is Us,” and Frat Boy Harry

By the end of 2013, One Direction had two internationally best-selling albums, having released” Midnight Memories” in November of that year. 1D also released “This Is Us” in 2013, a concert documentary film that was a box office success and became the fourth highest-grossing concert documentary of all time. 2013 was a big year for One Direction, but it was also a big year for anyone who loved Harry Styles, as a new Harry era was born. Harry was no longer the “flirt” of One Direction, but was now the “playboy,” and yet again, his clothes reflected this.

“Frat Boy Harry,” as many Harry stans affectionately called him, had emerged. The button-downs he practically trademarked were now left half-buttoned and displaying the iconic butterfly tattoo on his stomach. His now chin-length hair was swept back in stylish hats and beanies. He wore cutoff t-shirts, flannels and bandanas and he was dangerously handsome. This year was a very fashionable one for Harry, to say the absolute least.

The half-buttoned shirt, the chain, the hat, the ring on his middle finger; there is just so much to unpack here. This look is effortlessly cool and laid back, which is exactly what this era of Harry was all about.
Photo from pinterest.com
Not just one, but two flannels? Both unbuttoned? Harry knew exactly what he was doing with this look. If it were anyone else, two flannels would be blasphemous, but Harry made it work. Paired with the double chain, this look was a little busy pattern-wise, but worked because of how understated the rest of the pieces were.
Photo from pinterest.com
If one image ever summarized a frat bro’s sense of style, it’s this one. Harry wore a lot of jerseys in this era, from the Greenbay Packers to the Los Angeles Kings, to the Miami Heat, to the Lakers, as pictured here. Not a single man since then has ever been able to pull off a jersey or a bandana quite like Harry did.
Photo from pinterest.com

2014: The Beginning of Harry Styles as We Know Him

2014 was a pretty big year for One Direction. The group began their “Where We Are” tour in April of that year, released a third best-selling book, announced another concert film, dropped an autobiography and announced their fourth studio album, “Four.” By the end of 2014, Harry’s personal style started to shift to a more fashion-forward approach.

While he was still holding onto his then-coveted bandanas and half-buttoned shirts, by the end of the year he was starting to pick tasteful patterns over flannel and wore custom-tailored suits to events and galas. This year was a big one for 1D but was arguably an even bigger one for whoever was styling Harry.

This look seemed to embody the two styles that Harry was straddling in 2014. It was his usual half-buttoned button-up, but instead of a normal flannel, Harry picked a bold pattern that felt a little more fashionable. The loosely tied ascot and his simple jewelry really pulled this look together, and opened the doors for Harry to wear a variety of different designers in this year.
Image from teenvogue.com
Harry wore Saint Laurent to the 2014 AMA’s, and was just the beginning of Harry’s list of iconic suits. The gold embellishments on his jacket were only a hint of what was to come with Harry’s sense of dress, and the cheetah print boots were an understated but fashionable way to add to this suit.
Photo from pinterest.com
This Lanvin suit in December of 2014 solidified Harry’s role as the best-dressed member of 1D. Pinstripes are not for everyone, but if anyone could pull them off, it was Harry. This was not a look anyone would’ve imagined for a member of the world’s most popular boy band just four years prior, but as Harry has proven time and time again, he was not a typical member of a boy band.
Photo from pinterest.com

2015: The End of an Era

Every true Directioner remembers what a horrific day March 25, 2015 was. When Zayn announced he was leaving 1D, fans were left with a myriad of questions that were not fully answered until an appearance on James Corden’s “Late Late Show” that May, when One Direction appeared publicly as a foursome to announce they would not add a new fifth member and would continue with only Louis, Niall, Liam and Harry.

In lighter news, though, Harry’s hair was fully grown out, and while he was still wearing plain t-shirts, by this point his button-up game had totally upgraded and he was continuing his recent tradition of fabulous suits. This was a transitional time for the band, but also for Harry’s closet.

This silky bomber jacket by Saint Laurent was totally opposite of what the boys of 1D were sporting just five years earlier, but as the band changed, so did their clothes. Harry paired the intricate jacket with plain pants and his long hair, which was a show-stopper in itself.
Photo from pinterest.com
Fans oh-so-affectionately referred to this number for the 2015 AMA’s as his grandma’s couch, but honestly, it takes a certain kind of man to pull off a pastel, floral-patterned suit. Harry was no stranger to bold fashion choices, as he would later continue to prove.
Photo from pinterest.com
In December of 2015, One Direction went back to their “X-Factor” roots to perform for the show’s season finale, for the first time as a foursome. The Gucci suit Harry wore created a lot of controversies and he received quite a bit of backlash from both Directioners and viewers of “The X Factor” alike.
Photo from refinery29.com

2016: A Life Without One Direction

After releasing “Made in the A.M.” in 2015, their only album as a foursome, One Direction officially called it quits in January of 2016. This was, naturally, a pretty quiet year for Harry Styles, after five consecutive years spent directly in the spotlight. Harry co-wrote a song for Michael Bublé in 2016 and signed a recording contract with Columbia Records. Harry was featured on the cover of Another Man, a British fashion magazine, in 2016, where some of that years’ most notable Harry numbers were created, and where his style as we know it began to emerge.

Even when his red carpet looks were over-the-top formal, Harry’s street style remained pretty causal. In this candid from 2016, Harry wore another signature half-buttoned shirt with ripped, black jeans, simple jewelry and sunglasses.
Photo from pinterest.com
In 2016, Harry co-hosted a dinner to celebrate his Another Man covers with Alister Mackie and Kriss Van Assche. Wearing a simple and more understated Dior Homme suit (with another half-buttoned shirt underneath), Harry debuted his short hair to commemorate his magazine cover.
Photo from wmagazine.com
In one of many photos from his Another Man cover shoot, Harry looked edgy with his long hair styled very rock n’ roll and in yet another bold suit. This was just one of Harry’s several outfits for the 2016 fall/winter cover, and probably the most drastic one. Harry donned his classic, simple cross necklace and rings, this time with a thick, black choker and beat-up Converse sneakers.
Photo from Another Man Magazine

2017: “Dunkirk” and “Harry Styles”

2017 was arguably the most pivotal year of Harry’s career. Harry made his feature-film debut in Christopher Nolan’s “Dunkirk,” and released his self-titled debut solo album, featuring his single “Sign of the Times.” He was a musical guest on “SNL,” won a Brit Award, and appeared on “The Graham Norton Show” in the UK. Harry was no longer just a member of a popular boy band, he was a serious recording artist, and once again, his wardrobe was a reflection of this.

His clothes were no longer just the occasional print, pattern, bold accessory or bright color, but were now almost entirely just that. This era of Harry was a long time coming and was a major moment for him both professionally and artistically. 2017 brought us a new Harry, and with that came a new wardrobe, filled mostly with suits.

Harry’s affinity to Gucci has never been in question. This scarlet and black floral number was a showstopper at Radio Music Hall in September 2017, and for good reason. This brocade suit was classy and elevated, perfect for a show in one of the world’s most iconic venues.
Photo from vogue.com
Another day, another beautiful Gucci suit. Harry wore this blue floral ensemble in the LA leg of his first solo tour in 2017, paired with a loosely tied, oversized bow. This was outfit was a statement, to say the absolute least.
Photo from vogue.com
This Alexander McQueen suit deserves an entire article to itself. Nobody wears metallics, colors or patterns quite like Harry does. The muted shoe, delicate rings, and simple chain let the paisley do all the talking in this ensemble, as they should.
Photo from pinterest.com

2018: Gucci Gang, Literally

Harry Styles had not only re-asserted himself in the music scene by the end of 2017 but had almost completely reinvented himself. One Direction stans were not the only ones to notice this, either. In 2018, Harry began modeling for Gucci, appearing several of their campaigns. Harry finished out his first tour in July of this year, playing a total of 89 shows.

Harry continued to stunt in his now-signature suits, which were going absolutely nowhere any time soon. This era of Harry’s style has been described as almost gender fluid, as he dabbled in everything from glitter, shades of pink and purple, heeled shoes, frills and ruffles and bell sleeves and bottoms.

This picture belongs in the Louvre. Taking a brief break from his beloved Gucci, Harry wore this sparkly Saint Laurent number in Paris on tour. The silk shirt, the ruffle, the bare chest and the iconic chain paired so well with the glittery suit.
Photo from gq.com
Harry Styles in purple should be criminal. Harry donned this Calvin Klein ensemble to perform in Munich, pairing the bold suit with a black undershirt and sparkly heeled boots.
Photo from pinterest.com
This look comes from one of Harry’s 2018 Gucci ads, and surprisingly, it may be one of his simplest looks of the year. The understated gray suit was elevated by the plaid overcoat with fringe trim but felt causal when paired with the white and green sneakers.
Photo from pinterest.com

2019: New Music and the Met Gala

After the conclusion of his first tour, fans were anxiously awaiting new music from Harry. 2019 was the year prayers were answered, as Harry released the first single, “Lights Up,” from his second studio album, : Fine Line.” Featuring other singles such as “Watermelon Sugar,” “Adore You,” and “Falling,” “Fine Line” debuted at number three on the UK charts and topped the charts in the US.

The success of his first album and the budding anticipation of his sophomore album, as well as his work with Gucci and other courageous fashion endeavors, earned him not only an invitation to the 2019 Met Gala but the opportunity to co-host the event. Not only was this Harry’s first Met Gala, but he hosted in the company of celebrities like Serena Williams and Lady Gaga, as well as Gucci’s Alessandro Michele and of course, Anna Wintour herself.

The” Fine Line” cover album and photoshoot were ones for the history books. Harry, naturally, appeared in custom Gucci, fit for a king. As if the pink shirt were not statemented enough, Harry donned high waisted, double-breasted, buttoned bell bottoms. The patent leather shoes allowed the rest of the look to speak for itself, including the subtle fingernail polish.
Photo from nme.com
The 2019 Met Gala was undeniably one of Harry’s best looks of all time. Again, in custom Gucci, Harry turned heads in this sheer black number with an oversized pussy-bow and lace bell sleeves. The nail polish, dainty rings, heeled boots and all of Harry’s visible tattoos were simple elements that really heightened the look and paid tribute to ‘camp,’ the theme of 2019’s Met Gala.
Photo from pinterest.com
For the Met Gala’s after-party, hosted by Gucci, Harry made a costume change into a billowing sleeve shirt and oversized red bow tie and another pair of fitted black pants. The look was said to be inspired by the New Romantic era, which was popular in Europe during the 1980s.
Photo from vogue.com

2020: Riding the High of “Fine Line”

Ten years after his initial musical debut, Harry Styles is almost unrecognizable from the charming 16-year-old boy who sang “Isn’t She Lovely” for Simon Cowell. Harry has come a long way in a decade, from singing teeny-bopper pop hits to ballads comparable to that of Stevie Nicks. He is vocally, professionally and artistically a very different person than he was on “The X Factor.” This year, Harry has appeared in an NPR Tiny Desk Concert and released several music videos for the singles of “Fine Line” and was nominated for two Brit Awards. As always, Harry has delivered consistently unique and striking outfits for all of these milestones.

This year at the Brit Awards, Harry delivered an emotional performance of “Falling” in another custom Gucci look. This ornate white jumpsuit was several months in the making and felt fitting to Harry and his stylist to wear for this particular performance.
Photo from pinterest.com
Harry’s Tiny Desk Concert earlier this year was positively charming and gave him an outlet to share some of his music. His outfit, though, might have been the real star of the show. This graphic blue sweater was cheeky and different and paired nicely with the popped collar shirt underneath and grey pants.
Photo from pinterest.com
Just weeks ago, Harry dropped the “Watermelon Sugar” music video and left the internet in shambles. Harry wore several outfits in this video, all brightly colored and boldly patterned. The sunglasses pictured, and another similar pair a lá Elton John (which are for sale at Target for only $3), as well as knit tank tops, funky pants and fun jewelry add to the summertime vibe of the video and were fun ways to incorporate Harry’s sense of style.
Photo from pinterest.com

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