Harry Styles knows how to switch things up. Since making his debut at 16 years old, the One Direction singer has undergone massive style changes, outdoing himself every time as he leaned into the spotlight. Earlier years were marked by t-shirts and beanies, followed by skinny-ripped jeans and (unbuttoned) button-downs — the boyband uniform. As his solo career took off, he traded the muted greys, blues, and blacks of his wardrobe for colourful prints that only got bolder and louder as he embraced his now signature ‘’70s-nspired style. 

A good friend of Alessandro Michele’s, Styles was named Gucci ambassador in 2017. Not only did he wear Gucci for the 2019 Met Gala “Camp: Notes on Fashion”, he also joined hands with Michele for a collaborative collection titled “Gucci HA HA HA” in 2022. Unveiled at Milan Fashion Week, the collection featured tailored pieces layered with ‘70s references and whimsical touches. Think white buckled boots with a red heart print, funky leopard-print suitcases, and ripped wide-legged jeans. 

For Styles’ solo concert tour, Love On Tour, he dazzled on stage in custom Gucci looks designed by Alessandro Michele, with the help of stylist Harry Lambert. Among the tassels and paillettes to overalls galore, one outfit stole the spotlight: Styles’ Gucci Dorothy costume, complete with a bejewelled gingham skirt, red sparkly heels, and a bow — it was “Harryween,” after all.

In 2021, Styles co-founded the beauty and lifestyle brand Pleasing. Known for its vibrant nail polishes — an extension of his bold and expressive style — the brand also collaborated with fashion giant Jonathan Anderson to create timeless pieces representative of both creatives. Cream cardigans were reimagined with technicolour balloon embroidery, a playful nod to the JW Anderson patchwork cardigan Styles famously wore in 2020, while Pleasing sweatshirts were updated with  JW Anderson’s hallmark mylar star. Harry Styles has evolved from a musician to a creative powerhouse, armed with an artistic vision that effortlessly transcends genres.

Harry Styles in S.S. Dayley

An investor in British brand SS Daley, Harry Styles wears the brand’s Chore Jacket and handmade crochet strawberry brooch (handmade by Katherine) to the Spring/Summer 2025 womenswear show. 

Harry Styles in Egon Lab x Swarovski 

For the 2023 Grammy Awards, Styles wears a Swarovski-encrusted (25,000 crystals), diamond-patterned jumpsuit from Egonlab which took over 150 hours to create.