Harry Styles is the fashion icon of a generation, and we can prove it

Image via Gucci
Words by Maeve Kerr-Crowley

A bona fide sartorial tastemaker.

Harry Styles is one of the most fashion-forward, headline-inciting men currently in the game. This isn’t news, and very few people would even bother to argue the point.

So, what I’m going to argue instead is that Harry Styles has perfected – perhaps more than any star of his generation – the art of staying just one step ahead. For the entirety of his career, he’s gone just far enough with his style to stand out and keep people’s attention, but not far enough to freak out the masses. He’s changed with the times and aged with his fans, pulling us like swooning puppets along for the ride.

It’s a brand of stealthy rule-breaking that’s taken him from clean-cut, dimpled boyband member to gender-bending weirdo rockstar without any significant dips in his solid, loyal fan base.

Please, let me show you how, with a nine-year deep dive into Harry Styles’ style evolution.

2010 – The X Factor Era

Let’s get it out of the way quickly, and admit that this entire fashion experience was a train wreck. But, while beanies, cardigans and spindly scarves may have been the absolute worst the new decade had to offer, nobody who saw Harry’s auditions could deny his looks were memorable. Considering he dropped the scarves pretty quickly after making it on the show, I’m willing to extend enough credit and call this era a genius marketing move by an unacknowledged fashion prodigy.

2011 – The Boyfriend Era

This is the most accessible, non-threatening age of Harry. With a largely teenage, potentially fickle fan base at his fingertips, this wasn’t the time to be taking any big risks. But, unwilling to blend in too much, he always found ways to distinguish himself. His hair was bouncier, his shirts tighter, his colours poppier, all marking him as the most put together, sartorially in-the-know member of the group.

2012 – The Blazer Era

We saw touches of this Harry in the boyfriend era, but 2012 was when he really upped the game on his clean-cut but approachable gentleman’s persona. Every day it was blazers, alternating between neutral shades and rainbow hues. It was this sense of being slightly overdressed at all times that signalled – although we didn’t know it at the time – that he was destined to leave the rest of the band in the dust.

2013 – The Unbuttoned Era

Did this shift take you by surprise? It shouldn’t have. With Harry’s teenybopper fans getting older, they were practically begging for the first signs of his eccentric rockstar side. Boundaries were pushed as his boots got pointier, his hands and neck were decked out in jewellery, and more and more buttons were left tantalisingly undone. 

2014 – The Slightly More Unbuttoned Era

Yes, somehow Harry’s necklines crept further and further downward, his belly button symbolic of his fully-fledged fashion potential: both so, so close to peeking through satiny curtains and wowing the world. The ‘Steal My Girl’ music video is a great example of this turning point. That life-changing leopard print jacket was a cheeky taste of what was to come, that slightly too-long hair a sign of the personal growth we were unwittingly witnessing.

2015 – The Long Hair Era

Also known as the Post-Zayn Era. With the Bradford Bad Boy out of the picture, Harry had room to become his own kind of bad boy, the kind where looking like a boy really didn’t matter at all. With his hair reaching almost to the peak of his plunging necklines, and his shirts more wildly patterned or lushly textured than ever before, this was the age of Harry making you want to reach out and touch him – only to realise your own dirty, mortal hands weren’t worthy. 

2016 – The Cover Star Era

All pretences cast aside, Harry stepped into the light and told us we were really playing the fashion game, now. His absolute game-changer of a cover story for Another Man showed us a Harry so playful and versatile that it shouldn’t have been possible. Whether sporting a bowl cut and fuzzy sweater, or shirtless in a leather collar and military-inspired jacket, the exposé practically scolded us for even thinking of putting Harry in a box.

2017 – The Gucci Era Part 1

Here, Harry started splashing around in the Gucci pool he would soon be swimming laps in, rocking crisp, satiny, floral creations on the regular. That shining blue brocade from the ‘Kiwi’ video firmly established that Harry Styles: Solo Act was a very fancy, very pretty guy. Even his curly locks were tamed to let these outfits shine, although I’m convinced he knew the world was outgrowing its long hair obsession, and did what was necessary to avoid ever falling behind.

2018 – The Gucci Era Part 2

At first indistinguishable from The Gucci Era Part 1, it takes only a studying glance to note the distinction. This phase relied on a far more relaxed energy than its previous incarnation, filing down those sharp tailored edges into something looser and more feminine. Somehow, Harry found a way to combine the expensive cleanliness of GEP1 with the sloppy rockstar quality of the longstanding Unbuttoned Era.

2019 – Today

With only half a year under our belts, I’m reluctant to classify this era too firmly. That being said, we’re already seeing further shifts and evolutions, despite Harry being relatively quiet in the music world. Swinging wildly between chiffon and pearls for the Met Gala, and shirtless and scruffy for the cover of Rolling Stone, this seems like a year for playing with silhouettes, retrofits and the confines of masculinity more than ever before. Personally, I do think he can take it further, using his significant power and influence to help abolish our ideas of gendered dressing once and for all.

But maybe that’s the vibe for 2020.


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