They say the best way to heal a broken heart is in the arms of another, but the “Adore You” singer is taking a different method by encroaching on the eternal city—because what does a casual fling have on a bowl of Cacio e Pepe in the city that invented the piquant dish? While Styles was in town, the star rekindled one of his longest-standing relationships with recently appointed Valentino creative director, Alessandro Michele.

Harry Styles with Alessandro Michele in 2022 to announce their ‘HA HA HA’ collection. Credit: Instagram/@alessandro_michele

Naturally, this news has perked sartorialists’ ears with the late-night rendezvous potentially hinting at Styles’ allegiance firmly in Michele’s court—not the atelier of whichever maison he works for. Michele picked up the mantle of artistic lead at Valentino following Pierpaolo Piccioli’s shocking departure after 25 years at the helm. (The first thing Piccoli did after his contract was terminated was take a shopping spree at Gucci, toting a fistful of Ancora red shopping bags like the poet Virgil with an olive branch.) For the uninitiated, Alessandro Michele was replaced at Gucci by Piccoli’s former right-hand man, Sabato De Sarno, following his surprising stage right exit.

Michele’s time at Gucci was marked by unbridled romanticism and maximalism, and it was these traits that were parlayed onto Styles’ stage outfits for his new solo era. Michele helped Styles shed a bad boy image of Saint Laurent skinny jeans and step into the glam rock star he’s become. The kindred spirits honoured their relationship with a collection titled ‘HA HA HA’—quite literally an abbreviation of their first names—a capsule of dandy suits and eccentric storybook separates the duo dubbed as their ‘dream wardrobe’.

Though this duo is more a sartorial relationship and friendship than anything else, Styles and Michele did take a page out of the couple dressing rule book by wearing matching blue button-down shirts, slacks and black shoes. (Michele’s were Oxfords, Styles’ were Vans). Whether this reunion was a case of old friends reconnecting or a soft launch of something deeper, we’ll have our eyes on Valentino’s front row come September to see which of Michele’s acolytes, like Styles, have crossed over into this new era. Until then, we’ll be refreshing feeds for more Harry Styles in Italy content!