Harry Styles: Looking back at outfits that have made the singer and actor the world’s most stylish man

Harry Styles is just one of those lucky individuals who is innately stylish. Yes, he may have the help of a few stylists here and there, but he still undeniably knows how to dress well.

In other words, he has star quality. Harry has recently unveiled the HA HA HA collection in collaboration with Gucci. The iconic fashion house revealed that the collaboration came about because of the friendship between Harry and Gucci’s Creative Director Alessandro Michele.

On Gucci’s website, it reveals that “the series of Images sees Harry Styles showcase the ‘dream wardrobe’ defined by the eccentric use of romantic accents, whimsical prints, vintage details and the expressive emotionality of the individual.”

The photographs, which were taken by Mark Borthwick, show Harry dressed in a series of effortlessly cool pieces such as a Herringbone jacket and a Prince of Wales hat. Harry’s pale blue painted nails work effortlessly well alongside the eclectic pieces.

So, when and how did Harry Styles become the world’s most stylish man?

Harry first appeared on our screens at the tender age of 16 when he auditioned for The X Factor in 2010. He impressed the judges with a version of Stevie Wonder’s ‘Isn’t She Lovely.’

Harry’s outfit for his first audition may only have been a white t-shirt with a grey cardigan and black jeans, but it was his casually tied scarf around his neck that first gave the world an indication of his style credentials. When he first became a part of the boyband One Direction, the attention was naturally focused on the band rather than just him.

However, towards the end of his time with the band, he became renowned for his funky suits and love of bold colours.

He also started experimenting with his hair and getting a few tattoos, such as a cross tattoo on his hand.

In 2017, he wore a vibrant pink suit (very much in the style of Mick Jagger) while performing in New York City.

In 2020, he turned up to The BRITs in a chocolate brown suit, purple sweater and a pearl necklace round his neck. It was certainly different but undeniably stylish.

Harry Styles has been working with fashion house Gucci for a number of years, and it was way back in 2015 that stylist Harry Lambert decided Harry should try something new.

He dressed him in a floral suit from Michele’s spring/summer 2016 collection for the American Music Awards in November 2015. Harry was the first celebrity to wear one of Alessandro’s full menswear looks from the catwalk on the red carpet.

Since then, Harry and Gucci have continued to work together. More recently, Harry Styles looked incredibly stylish when he wore a Black Gucci suit at the ‘My Policeman Premiere.’

One of my favourite Harry’s looks to date though has to be the striped jacket he wore from his ‘HA HA HA’ collaboration with Gucci, along with flared trousers, at the 2022 Venice Film Festival. It was very cool and just so Harry.