Today in Milan, Gucci creative director Alessandro Michele held a press conference in a vintage clothing shop. The surprise announcement? A capsule collection, dubbed HA HA HA, that he designed with pop star and fashion muse Harry Styles.

The 25-look collection represents a mashup of the clothes the two friends love to wear—as Michele put it, their“dream wardrobe.” The designer said that the collaboration grew out of years of conversations over the phone, via WhatsApp, and over glasses of wine on the rare occasions they were in the same city. “It started just like two kids playing, you know, in a very easy way,” he said, adding that the collection “started to be something really concrete maybe one year ago.” The clothes took shape through mutual creative exchange rather than formal design meetings. “It’s more about life, you know? ’Cause when you are very encountered with someone in a very deep way, there is not really a way to do it. It’s just something that happened,” Michele said.

HA HA HA marks the deepest collaboration yet between Gucci and Styles. The 28-year-old has appeared in Gucci campaigns, and wears the brand extensively. But Styles is not just a celebrity with a contract: his fandom of the brand and admiration for Michele is real. When they met, Styles was a teenager who had just left One Direction to strike out on a solo career, and Michele had just taken over Gucci. “We grew together,” said Michele, who credits Styles with helping him reconnect with his teenage side. In recent years, Styles has become nothing less than the public avatar of Michele’s sensitive, genderless vision, and his genuine interest in clothing has only deepened. The only thing left for Styles to do with Gucci, really, was design his own collection. “The level that Harry has got now, it’s a high level perception of this job,” Michele said. In other words, it’s not a gimmick.

Michele’s ’70s-inspired tailoring silhouettes make up the backbone of the collection, with kicky flared trousers that Styles can take full credit for mainstreaming. Styles, in turn, “brought himself,” Michele said. “He always has in his mind a very sophisticated way to be a guy, you know?” The result, Michele said, is deeply personal, a collection that he described as “private and very cozy.” It’s what someone would find, basically, if you threw open the doors of either of their closets.

First up: several overcoats and blazers tailored with British club checks, Glen plaids, and pinstripes, a notable departure from Gucci’s typical baroque fabrics. A patchwork leather jacket, meanwhile, looked well at home on the racks of the vintage shop where the collection was presented. The venue reflected a mutual obsession with vintage shopping. “I love vintage shopping. I think that is really my place. Harry loves vintage too. We are crazy for vintage, both of us,” Michele said. There were also bright, poppy sweaters of the kind Styles has worn for years. Styles brought newsboy caps to the table, and Michele brought pajamas, some printed with hearts, others with a grumpy bear character. “They are something that I usually wear, and [Harry] started to wear too, and now he is obsessed with pajamas,” Michele said.