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How to dress as well as Harry Styles, the men’s style icon who breaks all the rules

“Clothes are there to have fun with and experiment with and play with,” is how Harry Styles, one of the best-dressed men of today, describes his style philosophy.

Indeed, the English rockstar has expressed that irreverent attitude with panache through his outfits, whether he’s out on a date with Olivia Wilde in a pair of ripped jeans and beat-up sneakers, fronting magazine covers in dresses, or showing up on the red carpet in pearls, feather boas, or a pair of Mary Jane shoes.

Pay close attention, though, and you’ll see that there is a formula to all that rule-breaking fashion. For one, Styles is constantly referencing his musical idols, like David Bowie, Elton John, and most obviously, Mick Jagger. Then there’s the fact that he’s an ambassador for Gucci, a luxury brand that champions extravagance and genderless dressing. And once you get your hands on his style essentials (Styles essentials?), all that’s really left is mastering the singer’s spunk.

We can’t help you with the latter, but we’ve made a list of everything you’ll find in heavy rotation in the Wardrobe of Harry Styles. Shop them below.

(Hero and featured image credits: Helene Marie Pambrun) 

1

When he gets on stage, Styles like to make a bold statement through tailoring. His choice of blazers is certainly more adventurous than the red carpet variety, with velvets, glitter, vintage checks and bright pops of colour thrown into the mix. This yellow linen jacket, fully lined in silk, can be worn with similar bravado and without any fuss of breaking a sweat. Layer it over a white tee and jeans if you’re going for “smart casual.”

Price
S$3,472
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2

Styles showed up to the 2021 Brit Awards with this Gucci bamboo handle bag in tow, an archival design that has also been favoured by Elizabeth Taylor, Rihanna and Beyoncé. Take it with you when you get all suited up like Styles, or wear it as crossbody on T-shirt-and-jeans days.

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S$2,576
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3

On his off days, Styles dresses down in vintage band tees showcasing his love for acts like Beastie Boys, Pink Floyd and The Rolling Stones. If you don’t have any music merch yourself, a printed graphic tee like this one would make a decent substitute.

Price
S$77
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4

Styles makes no secret of his love for florals, wearing patterned blazers on stage and chilling out in Hawaiian shirts on vacation. You can recreate the latter with this Drôle de Monsieur shirt, cut in a relaxed, boxy silhouette from a lightweight blend of linen and rayon.

Price
S$365
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5

Feeling chilly? Styles’ solution is to throw on a cardigan, much like the JW Anderson patchwork knit that he wore during a performance. The piece is sold out, but you can either a) knit your own, like the singer’s fans on TikTok, or b) get this similar colourblocked one crafted from cotton and wool.

Price
S$2,189
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6

Nothing captures a devil-may-care attitude like a pair of ripped jeans, and Styles likes his denim in a loose, wide-leg cut. This bestselling Balenciaga pair hits the mark, and we can already picture the Watermelon Sugar singer wearing it with an old-school band T-shirt.

Price
S$1,981
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7

Styles is a big fan of his Reebok Classics Club C sneakers, and we’re betting it has to do with how they echo the laid-back trainers of the past. You can wear a brand new pair until it gets scruffy, or simply get the leather kicks in this off-white shade.

Price
S$196
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8

Chelsea boots are one of Styles’ favourite footwear styles — naturally, given that they’re a staple of British menswear. He has sported several designs by Saint Laurent, including this elegant Wyatt pair sculpted from buffed calfskin leather.

Price
S$1,318
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9

Grunge icon Kurt Cobain is another source of inspiration for Styles, who has been spotted in round, white sunglasses much like the pair that the Nirvana frontman famously wore. Get the look with this homage by Tokyo fashion label Ambush.

Price
S$460
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10

For a finishing touch, throw all gender conventions out the window and adorn your neck with pearls, just as Styles, A$AP Rocky and Jaden Smith have all done.

Price
S$539
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Pameyla Cambe
Senior Writer
Pameyla Cambe is a fashion and jewellery writer who believes that style and substance shouldn't be mutually exclusive. She makes sense of the world through Gothic novels, horror films and music. Lots of music.