Harry Styles's ever-evolving style took another slight turn this year as the singer seemed to settle into what he likes and feels comfortable in. Harry has taken a large step away from the skinny jeans and t-shirts of his younger years and instead now wears looser silhouettes in bold colours and prints [1], most often conceptualised by friend and Gucci creative director Alessandro Michele. While we've seen him wearing more and more patterned suits on stage, this year he's evolved his style even more to be an everyday thing — wide-leg pants, soft yet stylish tees, and comfortable footwear are his staples. He wraps up all his looks with hands full of rings and pretty painted nails [2].
For a glimpse at Harry's best outfits from this year, keep reading ahead. I'm going to warn you now that it's almost all custom Gucci, and I'm not mad about it at all.
Harry Styles in March 2019
Harry started his fashion-forward year with a bang in this royal blue double-breasted Gucci suit to induct Stevie Nicks into the Rock and Roll Hall of Fame [4]. The velvet wide-leg suit is just one of many, many Gucci looks Harry's been rocking as of late.
Harry Styles in May 2019
Continuing his penchant for velvet, Harry stepped out in New York in this custom red Gucci suit jacket that made him look so damn luxe. He paired it with a low-cut white shirt and wide-leg black pants for the perfect night-out ensemble.
Harry Styles in May 2019
There's a lot to appreciate about Harry's custom Gucci Met Gala look [5]. The best parts are arguably the sheer black shirt with buttons down the back and his single drop pearl earring.
Harry Styles in May 2019
It should come as no surprise that Harry showed up to the Gucci 2020 Cruise fashion show in Italy in head-to-toe Gucci, including this darling bag [6]. What really popped about his monochromatic look, though, were those pink sunglasses.
Harry Styles in October 2019
Harry pulled out his suit from the 2017 Dunkirk premiere for an October even in London. The custom Gucci look fits him ever so perfectly, but the slick red Gucci boots, emblazoned with the word "Sucker" on the back really cap off this outfit.
Harry Styles in October 2019
If you're going to be on stage with Kacey Musgraves [7], you've gotta show up in style. Harry did just that in yet another custom Gucci look, with billowy high-waisted black pants and a soft and billowy black shirt.
Harry Styles in November 2019
This look is a lot, and it's all so very good. Harry very boldly donned this Lanvin sheep-print sweater vest [8] for a dinner out in New York, and it might be the best thing he's ever worn. He mixed all his prints, with a striped Gucci shirt and striped Gucci pants, and tied the whole look together with pink Gucci boots.
Harry Styles in November 2019
I love Harry in yellow, and these Gucci pants are no exception to that statement. Harry wore this colorblock look during his double-duty stint on Saturday Night Live [9].
Harry Styles in November 2019
For his "Lights Up" performance on SNL [10], Harry chose a custom Gucci jumpsuit that sparkled in shone in the stage lights. The cut of it perfectly showed off all his best assets, including his chest ink [11].
Harry Styles in November 2019
While some of us might opt for sweatpants and baggy t-shirts for a cross-country flight, Harry instead opts for Gucci jeans and a soft red t-shirt. While traipsing through a New York airport, Harry also topped the whole look with this stylish denim jacket from The Vintage Showroom [12] in London.
Harry Styles in December 2019
I'm obsessed with this Alled-Martinez jumpsuit that the design house custom made for Harry for the Jingle Bell Ball in London. It's based on the look he wore for Rolling Stone earlier in the year, but this time the denim outfit is all one piece — with the addition of sparkles. With the top open just down to there so his butterfly tattoo is on display? Yep, this one's a winner.
Harry Styles in December 2019
We love a guy who believes in his own merch [13]. For his BBC Radio 1 Live Lounge appearance [14], Harry wore his own shirt that he designed with Gucci Creative Director Alessandro Michele and topped it off with the same string of pearls he's been wearing as of late.