a guide to harry styles’ fashion evolution

From Jack Wills hoodies to custom-made Charles Jeffrey Loverboy jumpsuits.

by Douglas Greenwood
26 September 2018, 3:42pm

Ever since he first burst onto the X Factor stage eight years ago -- a secondary school student and part-time baker with the boyish good looks of a pre-made pop star -- everybody has found Harry Styles to be disarmingly charming. He was that old, outdated trope brought to life: teenagers either wanted to be him, or be with him. But so much has changed since those sweet wholesome drop-crotch chino days. Harry, like the rest of his 1D peers, has grown up, and with it so has his sense of style.

Having swapped out Jack Wills gilets for Gucci campaigns (the kind that can throw the internet into meltdown faster than you can say ‘pop star nestling a pig’) his fashion sense can now best be described as something like... New Romantic Alessandro Michele Genderfluid Modern Rockstar. It mustn’t go unmentioned that this is in large part down to one of fashion’s most sought after stylists: the brilliant Harry Lambert. It’s because of their creative union that Styles dropped Camden Market shearling jackets and Chelsea boots for custom one-pieces from CSM designers and Gucci loafers.

Here’s a deep dive into his style evolution. It's what we deserve.

2010: The Purple Hoodie Moment
It’s a little known fact that, in the early 2010s, sales of purple hoodies hit an all-time high, and they’ve never quite reached such heady levels of fashion success since.

Think about it: on both sides of the Atlantic, the biggest male pop stars of our generation were causing a mini fashion-revolution that was trickling down through high schools up and down the country. Stateside, Bieber was rocking that amethyst American Apparel number for what felt like a whole damn press tour, while our Harry popped out to the Sainsbury’s wearing the Brit equivalent: a logo-emblazoned Jack Wills one. Pair it with the low-slung jeans and this look epitomizes 2010.

2012: The Brit Awards
Two years have passed. One Direction, much to our dismay, didn’t win The X Factor, but Harry and his bandmates got the last laugh by sauntering off and signing a lucrative record deal anyway. Unlike the vast majority of reality TV grads, 1D have made it big -- like stratospherically big -- and so there are stylists making strong fashion calls for them now.

Before the charcoal grey suit became the go-to look for teenagers at weddings they didn’t want to be at, Harry rocked up to The Brit Awards in 2012 wearing a three-piece one, pulling it off flawlessly. He looked dangerously dapper, but it’s the droopy black bow-tie, almost reminiscent of a pussy bow, that caught our eye with this one. It’s like a little nod to the looks that’ll inform his style in future.

2014: Glimmers of a future rockstar
By the time 2014 came around, Harry’s pop star facade was starting to crack. The fashion press were starting to notice that the now-20-year-old was gaining a Jagger-esque reputation, and his fashion decisions were startling to reflect this butterfly emerging from the chrysalis.

His tattooed skin was now a little more on show, peering out from beneath unbuttoned paisley shirts. His hair was getting longer, slicked back, and kept in place by paisley scarves. The jeans were skinnier than they had ever been before.

He jumped on stage with his bandmates at Radio 1’s Big Weekend in Glasgow that summer, upgrading his high street fashion looks to a more luxe territory with a Calvin Klein sweatshirt, black skinny jeans, and heeled suede camel boots. At this point, just as 1D were starting to put a halt to their illustrious career, Harry’s squeaky-clean image started to disintegrate, and a fresh rockstar emerge from its shell.

2016: Shearling, new beginnings, and the hair switch up
At the start of 2016, One Direction went on an indefinite hiatus, and the rumors of what each member would do next were talking points for pop culture fanatics for the months that followed. While most of his peers went off into big TV appearances and pre-packed solo careers, Styles took time to slip out of the spotlight, avoiding red carpet gigs for a bit.

As a result, we only really saw glimmers of this limbo stage in paparazzi photos of Harry pottering about London, New York and LA.

His hair was at its longest here, but not for long: mere months after this shot, Harry was cast in Christopher Nolan’s Dunkirk, and chopped it short at the director’s request.

Early 2017: The Loverboy
After nearly 18 months of musical silence, Harry returned in the spring of 2017 with a switched-up sound. Marked by his single Sign of the Times, it came with a series of looks -- selected for him by Harry Lambert -- that would reposition pop’s gentle bad boy as a new kind of star: a compassionate one with a flamboyant, sexy, and Bowie-worthy dress sense.

As the promo tour rolled out, the boy who once felt most comfortable wearing a purple Jack Wills hoodie rocked up to The Late Late Show in the US wearing a padded pinstripe jumpsuit by Charles Jeffrey Loverboy. With its double-breasted top half and billowing trouser legs, it felt like a wild, semi-androgynous change of scene. Little did we know it would lead us into one of the most delicious tour wardrobes of the year.

2018: New Romantic on the road
Harry Lambert’s appreciation of punkish and youthful designers (paired with a soon-to-be-announced link-up with Gucci) meant that Styles rocked up in a different city every night on his tour wearing a new custom tailored suit.

Even though his style -- both physically and sonically -- has changed, Harry still harbors the power to propel anyone he’s associated with into the spotlight. Case in point: the LA-born but now London-based designer and Central Saint Martins student Harris Reed. When Lambert reached out to him earlier in the year to create a look for Styles’ show in Amsterdam, Reed, still just 21 years old and having never completed a custom look for a client before, crafted a bespoke outfit that’s rightfully earned a place in the Styles fashion history.

The look, comprised of a three-tiered ruffled blouse and ostentatious flares, proved that Harry was willing to step into grandiose territory with his outfits now. He’s the next gen New Romantic, and his fashion choices were getting more exciting with each new move.

2018: Gucci Gang
From a humdrum childhood in a quaint Cheshire town, to this. In 2018, we learned that Harry would become the new face of Gucci Cruise’s tailoring line.

Gucci took Harry to a quintessential English chip shop for the first campaign, before sprucing things up for the second. Set in Villa Lante, a historic hotspot just outside Rome, the shots saw Harry accessorise with adorable baby farm animals and an array of enchanting tailored pieces.

The extreme lapels, clashing checks and embellished brooch pieces we’ve come to associate with Gucci’s wunderkind Alessandro Michele now look like everyday items in Harry’s burgeoning wardrobe. But there is one piece that stands out, and it’s simple: a gold crown of thorns, resting upon his head like the certified prince of pop star fashion. Long may he rule.

This article originally appeared on i-D UK.

Charles Jeffrey
One Direction
Harry Styles
celebrity style
harris reed