The Grammys plotlines ran surprisingly deep this year. There was serious (and well-deserved) hardware for DeBÍ TiRAR MáS FOToS, a stacked Best New Artist category, the constant threat of Timothée Chalamet. But of all the celebrity machinations, it was a single, notable appearance that really made the night special — a semi-surprise showing by the one and only Harold Stylish.
Every Menswear Look From the Grammys 2026 Red Carpet
Big ‘fits from music’s biggest hitsTo be clear, Harry Styles at the Grammys is not a surprise. The musician-actor has long been a familiar sight at the awards show — the three-time winner was omnipresent during the early 2020s. But, since releasing Harry’s House in 2022, Style’s antics have skewed monkish; beyond his blisteringly fast incognito marathons, he’s generally managed to recuse himself from the glaring limelight.
That was, of course, until last month’s much-anticipated announcement of his forthcoming album Kiss All the Time. Disco, Occasionally, a seemingly clubby, house-adjacent project set to be released in early March. Beyond rocketing Styles back into the public consciousness, it might help explain his presence at the Grammys last night, where he took to the stage to hand out the Album of the Year, a prize that would ultimately go to Bad Bunny.
Although absent from the official red carpet, Styles is never one to shy away from a ‘fit, and he took full advantage of the Grammys’ loose-ish dress code while presenting the award. In seeming homage to his new dancehall aesthetic, the actor took to the stage in what might be aptly described as tuxedo-tailoring-meets-techno, sporting a (ready for this?) nipped-waist, peak-lapel, semi-sparkly matte grey double-breasted Bar jacket, sans shirt and oozing with retro pop icon swagger.
Not to be bogged down by bespoke codes, Styles completed the outfit with a pair of $1,150 normcore dark-wash straight-leg jeans, minimal accessories that included Style’s daily driver Cartier Tank and mint-green ballet flats from Dior’s Spring 2026 collection, finished with bow laces and reminiscent of the torpedo silhouette the musician has been rocking as of late, most notably in the music video for his recent single “Aperture.”
While instantly reminiscent of his flamboyant personal style, the pairing of a cropped, highly structured jacket with bust-a-move denim felt decidedly different — more mature? — than Styles’s previous Grammy looks, with an intense and evident focus on craft and tailoring and a high-low vibe more akin to socialite club rat than international pop star.
The club-coded look, styled by longtime collaborator Harry Lambert, might look familiar to eagle-eyed fashion fans, and for good reason. The entire outfit is custom-designed by none other than Jonathan Anderson, who rocked Paris Fashion Week with a similarly bedazzled Dior Autumn 2026 menswear collection just days ago with similarly cropped Bar jackets.
Styles’s Dior debut is a bit of a departure from his previous designer inclinations — long a muse for legendary designer Alessandro Michele at Gucci and Valentino, the actor has been more recently celebrated for his wholehearted embrace of Mary Kate and Ashley Olsen’s The Row, a cultish, minimalist design label renowned for its impossibly chic cuts and astronomical pricing.
Is this embrace of Anderson’s Dior a hint at a new, sexier, messier era of pop star sartorialism for Styles, or a one-off occasion? Only time — and the album rollout — will tell. For now, just bask in the glow.
More Like This
This article appeared in an InsideHook newsletter. Sign up for free to get more on travel, wellness, style, drinking, and culture.