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Harry Styles' Best Looks Over the Years

Dressing up for himself, and getting up onto best-dressed lists

By Paddy Maddison and Carmen Bellot
harry styles best style moments
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Ever heard of nominative determinism? No? Well, it’s the idea that people are subconsciously predisposed to do things that reflect their name in some way. If true, it could explain why Harry Styles has been topping best-dressed lists (and the Twitter trending list) for the fat end of the last five years.

Here, we take a look back and revisit some of the former One Directioner's most noteworthy fits.

1

Harry Styles Goes To The Movies!

harry styles wearing a suit
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A double-breasted Harry Styles suit isn't quite rock 'n' roll Harry Styles, but the Dunkirk actor's Cuban-heeled boot to the film's premiere very much were. Think Keith Richards, but at a wedding he was almost disinvited from.

2

Harry Styles Goes All Harlequin!

harry styles wearing a suit
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Head deep into Styles' wardrobe and eventually you'll emerge in a strange snowy land that bears a striking resemblance to the King's Road circa 1965. Here, you'll meet a curious creature - half goat, half Mick Jagger - who'll hand you today's outfit: harlequin-themed, Gucci, and with a Meat Loaf ruff.

3

Harry Styles Goes To Sir Gaernarfon!

harry styles wearing a jumper
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The pants of a portly Eighties stockbroker and a sweater vest à la Betws-y-Coed gift shop. It shouldn't work. And yet.

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4

Harry Styles Goes All Candid!

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Normally, Harry Styles floats above trends. But in the big barrel of statement knitwear, the 'Golden' boy is knee-deep in a printed Lanvin cardigan and muted slacks.

5

Harry Styles Goes Nowhere Without Security!

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Though a former Cowell protégé, Styles did not learn the high waistband from his old boss. This is better. Cooler, even – and largely because an X Factor stylist had nothing to do with it.

6

Harry Styles Goes Into The Studio!

harry styles nails
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Is Styles:

A) Leaving the BBC Radio 2 studio after appearing on Zoe Ball's breakfast show in 2020?

B) Emerging from a Jackie magazine cover shoot in 1976?

Wrong answers only.

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7

Harry Styles Goes For Gold! (Well, Yellow)

harry styles wearing a yellow suit
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Of the three looks Styles served us at this year’s Brit awards, this one was probably the most yellow. Channelling Mick Jagger once again, the Watermelon Sugar singer went full Peacock Revolution in a glowing Marc Jacobs suit previously worn by Lady Gaga.

8

Harry Styles Really Goes For It!

harry styles wearing a pink blazer, purple trousers matched with a blue shirt
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A generational divide has now been bridged, and across it stomps young women in love with Styles' Fifties TV host get-up and the old women who fell in love with it the first time round.

9

Harry Styles Goes For Tea With Your Nan!

harry styles wearing a blue jumper and green trousers
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Harry Styles is the sort of fella you could take home to meet your gran. In fact, he’s the sort of fella that dresses a bit like your nan. And thanks to pearls and colour pop knitwear and haunted Edwardian collars, so are we.

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10

Harry Styles Goes To The Met Gala!

harry styles at the met gala wearing gucci
Sean Zanni

The 2019 Met Gala was all about camp: a dress code inspired by Susan Sontag's seminal essay on "the psychopathology of affluence". Many guests missed the mark. Styles did not thanks to a little help from Gucci.

11

Harry Styles Goes To Venice!

venice, italy september 05 harry styles arrives for the photocall for dont worry darling during the 79th venice international film festival on september 05, 2022 in venice, italy photo by franco origliagetty images
Franco Origlia//Getty Images

What comes with an invite to Venice Film Festival? An outfit that speaks to the gondola-goers perusing the city. As part of the infamous Don’t Worry Darling tour, Styles balanced yachting attire (read: silk neckerchief and nautical-stripe blazer) with his signature ‘70s flares and yellow-tinted sunnies.

12

Harry Styles Goes Tinsel-Tastic!

los angeles february 5 harry styles at the 65th annual grammy awards, broadcasting live sunday, february 5, 2023 800 1130 pm, live et500 830 pm, live pt on the cbs television network, and available to stream live and on demand on paramount photo by francis speckercbs via getty images
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Tinsel isn’t just for Christmas; it’s outfit inspo for attention-grabbing Grammy performance costumes – well, for Harry it is. After donning this heavily-fringed Gucci onesie at the 65th awards ceremony, he’s had many questioning if they can fashion an outfit with the room-diving decoration. Not only does he top charts, but this look gives the classic tree-topper a run for its money.

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13

Harry Styles Goes Very L.A.!

new york, new york august 18 harry styles is seen on august 18, 2022 in new york city photo by gothamgc images
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So-Californication can happen to the best of us Brits, and it unsurprisingly happened to Styles. You could tell that the singer has a home in Los Angeles prior to seeing this outfit; it says everything you need to know. Loose, fashionably unkept curls; a sun-kissed tan; chest-baring crochet shirt: all the ingredients of a man who’s settled into the green juice-yielding lifestyle. And he pulls it off too.

14

Harry Styles Goes Green!

british singer actor harry styles arrives for the premiere of my policeman during the toronto international film festival in toronto, ontario, canada, on september 11, 2022 photo by geoff robins afp photo by geoff robinsafp via getty images
GEOFF ROBINS//Getty Images

There are a few reasons why you would be envious of Styles, but the want factor of this ensemble is enough to have you as green as the pieces themselves. From the Gucci Bamboo 1947 bag and emerald lily corsage to the trouser-matching nail polish (his brand Pleasing, no doubt), there’s enough to convince even the most prasinophobic to adopt some Grinch-hued accessories.

15

Harry Styles Goes Topless!

london, england february 11 editorial use only harry styles performs on stage during the brit awards 2023 at the o2 arena on february 11, 2023 in london, england photo by gareth cattermolegareth cattermolegetty images
Gareth Cattermole//Getty Images

Not many can go on best-dressed list for an absence of clothing… but Harry can! Especially when what’s covering him from complete torso nakedness is this cropped, sequin jacket. Who knew a piece resemblant of a circus ringmaster’s uniform could look great on stage at the Brits.

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