Style File: Harry Styles' Most Fashionable Moments

From One Direction to bonafide solo act, the British pop singer’s style evolution has also soared


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SEPTEMBER 2013

A blank slate. Before he's fully realised his potential and exposure to stylists and designers, here is Harry at the height of One Direction’s fame, wearing a classic rock n roll uniform of a white t-shirt and skinny black jeans, while on a night out in London.

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NOVEMBER 2015

In the twilight years with 1D, here is an early indication of what was to later come in regards to printed suits with a 70s silhouette. This wallpaper print showcases Harry’s flamboyant personality at the 2015 American Music Awards in L.A.

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JULY 2017

Going for a sleek sophisticated all black suit, Harry’s personality comes through with Western style embellishments on the trousers and a pair of steel cap boots at the New York premiere of his film Dunkirk. Like a modern day Johnny Cash, an all-black suit in the right fabric can be a great way to look put together for a special occasion and Harry nails it.

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SEPTEMBER 2017

Groovy. At the iHeartRadio Music Festival in Las Vegas, this is one of the first appearances of Harry wearing a full Gucci look, his go to red carpet label. Sorry Austin Powers, Harry wore it better.

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NOVEMBER 2017

Arriving in Sydney at the ARIA Awards, Harry’s confidence begins to bloom even more, opting for this paisley print Gucci suit in a light reflecting fabric.

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APRIL 2019

Two style icons side by side, Harry selects a bright cobalt blue suit from Gucci’s pre-fall 2019 collection to wear at the 2019 Rock & Roll Hall of Fame Induction Ceremony, where the Fleetwood Mac legend received her induction looking typically bewitching dressed in signature black.

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MAY 2019

One of Harry’s greatest style moments was as the co-chair for the 2019 Met Gala opening night for its exhibition Camp: Notes On Fashion, where he naturally wore Gucci, accompanied by creative director Alessandro Michele (pictured in the background). The look is a nod to Victorian gothic glamour, and Harry appropriately adheres to the camp dress code.

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NOVEMBER 2019

Off-duty Harry is just as great, this time out in Manhattan wearing a vest with sheep on it and a pair of wide leg navy trousers. A great cut on Harry, we see more wide leg trousers towards the end of the year and into the new decade.

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DECEMBER 2019

This is a another great example of Harry off-duty, wearing a t-shirt, plaid jacket and wide leg tan trousers which look good with a pair of crisp white canvas sneakers. Here we see remnants of his pearl earring at the Met Gala in May, this time in the form of a pearl necklace which gradually becomes a signature accessory.

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FEBRUARY 2020

Performing for daytime TV, this outfit is a great mix of colour, and especially like how the polka dot tie sits against a simple chambray shirt.

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FEBRUARY 2020

Like Fez from That 70s Show, Harry dons a stripe tee and a pair of brown corduroy flares while leaving the BBC Radio 2 Studios in London. His jacket is a great piece of outerwear, and his pearl necklace against a casual t-shirt becomes a signature look.

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FEBRUARY 2020

One of two great Gucci looks on the red carpet at the Brit Awards in London, the entire look right down to the Mary Jane shoes is a masterclass in subversion.

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MARCH 2020

No one else can wear a Peter Pan collar and pearls quite like Harry, and this colour blocking Gucci outfit is a joyful look during a visit to the SiriusXM Studios in New York.

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