Harry Styles’ Fashion Evolution Is Something to Behold — See 35 of His Best Looks Ever

2012

Admittedly, Harry’s early looks were mostly that of a young teen still uneducated and uncaring in the ways of fashion. It’s totally cool. He gets a pass. But this shot of him performing on the Today show in March 2012 basically encompasses a lot of his early onstage style — preppy and sweet.

This street style look from the same year showed one of two sides to his off-stage sensibilities — the bomber jacket with the white tee and chain give him a slight bad boy edge. Knowing the full breadth of his style in a few years time, it’s clearly the beginnings of something good.

The infamous Taylor Swift Central Park date, also in 2012, showed the other side of his casual style, a.k.a. the cozy, perfect boyfriend look. Many a teenage girl was indoctrinated into the Church of Harry Styles with this look — and this date. Haylor shippers still exist, y’all.

2013

See what we meant about the whole bad boy thing? H took the style cues he was receiving from the ~universe~ seriously and capitalized on a look that really suited him this year.

The move definitely paid off for him, because the hot rebel look worked perfectly for the Midnight Memories album era, which reintroduced the boys featuring a rock influence. Also, he started ~growing up~, which definitely didn’t hurt.

He also started to flex with some high fashion looks in the fall/winter season of 2013. His sleek all-black ensemble with the accent animal print top at the LFW Burberry show swept through the fashion world like wildfire — simple, understated, yet precisely on-trend.

He was making such a huge name for himself amongst fashion gurus, he closed out the year by taking home the British Style Award at the 2013 British Fashion Awards. Prestigious AF … and he hadn’t even come close to his style peak yet.

2014

The looks got better, the hair got longer. Harry took to wearing various different headscarves as he started to grow out his signature curls and skinny jeans continued to be a main fixture in the wardrobe in 2014.

H also started a nice collection of fedoras and wide brimmed hats this year — and singlehandedly contributed to bringing back neck scarves. And he did it all with a pair of Saint Laurent Wyatt boots on, an accessory he was rarely seen without.

But he also proved quite a few times that year that his event style was evolving, just like his casual style. The YSL ruffled collar blouse he wore to a film launch with Kate Moss at Annabel’s in London was a look rarely seen on a man, let alone one his age. It worked and it was charming — and a bit foreshadowing to the fashions of his later years.

This Saint Laurent leopard print denim jacket is just another example of something Harry loves: a statement piece. Kate Middleton seemed to dig the look, too, while meeting him at the Royal Variety Performance in London.

Patterned button-up shirts (and pants, but more on those later) started to cycle into H’s closet, pairing them with the signature skinnies and boots combo. Of course, he would often throw in one of those neck scarves only he could rock so well, as seen here during 1D’s appearance on the Today show in honor of the release of their album Four.

Generally speaking for Harry, ’14 was the year of designer Hedi Slimane‘s Saint Laurent, which was all about tight, sleek, distressed chic clothing. But he pulled out a few really elegant high fashion looks from the brand during this phase, too, including his stage ‘fit for the 2014 American Music Awards.

Kind of following in the footsteps of the Best Actor Academy Award, H showed up once again to the British Fashion Awards in 2104 to present the award he’d won the previous year to Emma Watson. His black and red pinstriped Lanvin suit reminded everyone why he won in the first place.

2015

As if the year had some kind of ~magical powers~, 2015 ushered in the true era of long haired Harry and all of his fashion fortitude really started to snowball into something huge. This YSL bomber jacket was one of those things. Yeah, it’s that cute.

He also started taking more fully formed fashion risks. Instead of always relying on smaller statement pieces, he started really playing with fully patterned suits — like this impeccable Gucci number he wore to the Love magazine and Miu Miu party for LFW. H’s stylist and friend, Harry Lambert, is the one looking up at him like a total dream in the corner of the shot, and like, what a mood.

But just because he was branching out and getting a little more experimental doesn’t mean he didn’t rely on his roots. Skinny jeans and boots were never far from his choice, but this pink and white polka dot Gucci shirt gave this look from the 2015 Apple Music Festival just a bit of flair. After all, who doesn’t love a man in pink?

And then there were some more refined, prince-like looks, like this London street ‘fit, that would pop up every now and again. Allusions to his preppy past would pop through, but with a clear cut influence from his (at the time) 21-year-old style.

When the boys rehearsed for Jimmy Kimmel Live in 2015, we’d literally never seen a man wear a shearling vest so well up until that point. It was a statement piece of a different breed — and, considering the outdoor performance was in the fall, probably kept him toasty, too.

Any time H goes with a color he’s not normally spotted in, it’s hard not to take notice. This off-stage look wasn’t exactly ~new territory~ but the choice of red makes this ‘fit a fave. He doesn’t wear it often, but red remains a great color for him.

In Harry’s Live at the BBC special from 2018, his friend, Nick Grimshaw, told him there is one unanimous look the world at large feels is his worst. H immediately, and correctly, guessed this Gucci one from the 2015 American Music Awards red carpet — and he was right. He went on to defend the ‘fit, saying he “thought it was good” and still does. So do we, babe. In fact, we think this statement suit is on of the best.

Later, in the press room, H toned in down a bit — or so it seemed. But his sparkly silver boots poking out from under his loose fit trousers reminded everyone what he was capable of, with the perfect little accent piece on his collar.

OK, OK, admittedly, this all-black look from the 2015 Jingle Ball performance seems way more basic than the rest … that is, until you notice the hand-embroidered ‘Styles’ over his heart.

2017

No shade on 2016 — 1D went on ~hiatus~ that year, so we’re still a little raw — but 2017 brought on a whole new Harry the world really needed. It was the start of his solo era and with that came some new fashion choices, ones that refused to stay entirely in the conventional. This pink Edward Sexton suit from his Today show performance promoting his first single, “Sign of the Times,” was a sign the singer’s style was still sound after a bit of time away from the spotlight.

On his way to the BBC to continue to promote the single, H pulled out this summery plaid suit from Vivienne Westwood, complete with heeled Gucci loafers, and the look was refreshing and refined. Classy, yet fun.

The same day, he pulled another casual look while rehearsing for a performance — and yeah, it doesn’t seem all that interesting but … have a look at the back.

On the red carpet for the world premiere of Dunkirk, both Harry’s first feature film and starring role, he went for an understated approach. Fans loved the clean-cut, sleek Gucci suit, which he paired with some sick Gucci accent boots.

Swallows on swallows! This embellished Stella McCartney blouse top seemed to be a call to the swallow tattoos Harry has on his chest, directly under their placement on the garment. Either way, it was another understated look with clear-cut fashion sensibilities. Plus, those Calvin Klein steel-toed boots are to die for.

During an appearance on the Tonight Show with his pal Jimmy Fallon, Harry brought out his best accessory ever. Paired with an all-black Alexander McQueen suit were his rainbow Gucci boots, an accessory he’s become synonymous with.

For the second show of H’s first solo tour ever, he gave Los Angeles a flowery treat. The floral suits became a staple on the road and we got to see so many lovely ones over the course of his two-part world tour. This particular one-of-a-kind Gucci number was so beautiful, it got a second life in Harry’s music video for his track, “Kiwi.”

We told you red was rare and special on Harry — which has to be why he chose this incredible one-of-a-kind Gucci beauty for his first tour stop in NYC. This Radio City Music Hall look was one for the books.

While soaking up the sun on tour in Australia, Harry attended the 2017 ARIA Awards and absolutely demolished any and all fashion competition with this psychedelic Alexander McQueen suit. And with good reason — he took home the award for Best International Artist, too.

2018

Fast forward to the 2018 leg of the tour and things started to get, well, leggy in H’s wardrobe. We started seeing the singer experimenting with some serious bell bottoms in another one-of-a-kind Gucci piece while performing at Madison Square Garden for his second NYC show.

Then Halloween came around and the kid served us one of his best ~lewks~ yet: a head-to-toe replica of Elton John‘s sequin-studded Dodgers uniform worn when he played the Los Angeles stadium back in 1975. The look is legendary and the world loved Harry’s rendition so much, even MLB.com wrote about it.

2019

We’re still early yet in 2019, so there’s time for more brilliance, but so far H has kept us a bit in the dark with his fashion sensibilities. He’s been seen out in workout clothes most often, which is cute, but it’s not his usual event fare. But we have a feeling there is greatness to come, judging by this fabulous royal blue Gucci suit he wore to induct close friend Stevie Nicks into the Rock and Roll Hall of Fame in March.