When he was a little boy, Charles Jeffrey, the designer behind the London label Charles Jeffrey Loverboy, thought that his mother was Madonna. The walls of his childhood Glaswegian home were adorned by his parents with framed images from the singer’s outré Sex book. “That’s your mum,” his father would tease the 5-year-old Jeffrey. “I think my mother and Madonna had similar peroxide hair,” Jeffrey says, laughing.

Composer and vocalist Jordan Hunt, choreographer and director Masumi Saito, and set designer Gary Card. Hunt wears Falke socks. Card wears an Emma Willis shirt.

Photograph by Tim Walker. Styled by Sara Moonves

Considering his early introduction to glamour and performance, ­Jeffrey’s obsession with challenging convention seems almost inevitable. Charles Jeffrey Loverboy started out as a monthly party that ­Jeffrey, who is now 28, began hosting in 2014 in East London, inspired by flamboyant, legendary 1980s clubs like Blitz and Taboo, where the likes of Boy George, Leigh Bowery, and John Galliano were regulars. Jeffrey describes the parties, which he hosted over a two-year run, as a “no-rules nocturnal laboratory” that brought together London’s young queer community and became a phenomenon thanks to theme nights such as “Strange Garden,” for which the dance floor was covered in mud. From this creative cauldron emerged Jeffrey’s riotous fashion line, now in its fifth season. “The clothes were made in that club space, and I learned a lot about being a queer person through being there,” he says.

Niall Underwood, the original muse for Charles Jeffrey Loverboy. Underwood wears a pin from Costume Studio Limited, London.

Photograph by Tim Walker. Styled by Sara Moonves

That’s not to say that those crazy nights were just about fun and games. In fact, they helped pay for Jeffrey’s master’s degree at Central Saint Martins, which followed a three-month internship in the haute couture ateliers of Christian Dior in Paris, while Jeffrey was pursuing his B.A. Those rigorous influences are clear in his wasp-waist suiting, artfully chaotic knits, painted denims, and what he refers to as his “nervous tailoring.” Befittingly, Galliano, his hero both as a designer and former nightclub denizen, presented him with the accolade of Emerging Menswear Designer of the Year at last year’s British Fashion Awards.

Drag performer and artist Benedict Douglas Stewardson. All wear Charles Jeffrey Loverboy clothing

Photograph by Tim Walker. Styled by Sara Moonves

Like Galliano, Jeffrey mixes everyday and highbrow references in his work. One of his favorite places is the Wallace Collection, known for its trove of 18th- and 19th-century French paintings. “It’s the best thing in London to do for free,” he exclaims as he struts through the galleries, wearing a reconstructed vintage suit and platform sneakers (think cyberpunk meets Spice Girl), his MAC-painted face rosier than those in the Gainsborough portraits on the walls. “It’s something I’ve always done since I watched an amazing documentary called Painted Ladies,” he says of his look, which has garnered the attention of superfans—“Loverboys”—who dress up or interpret his makeup on Instagram.

Lucas Nettleton-Tate. All wear Charles Jeffrey Loverboy clothing

Photograph by Tim Walker. Styled by Sara Moonves

Jeffrey’s latest collection, Tantrum!, offers mutant tartans, outsize argyle patterns, and suits ripped with rapier tears. The show was based on a book he deems required reading: The Velvet Rage: Overcoming the Pain of Growing Up Gay in a Straight Man’s World, by the American clinical psychologist Alan Downs. “Quite a lot was happening to me at a quick pace; one minute you are a student, and the next minute you’re the Pied Piper,” Jeffrey says, explaining that he drew from the dark frustrations of growing up bullied in Scotland. “I remember thinking as a kid, I’ll show them, I’ll be a fucking famous designer, that whole kind of thing. That attitude stays with you. It’s anger as energy.”

Charles Jeffrey (right) with collaborator and filmmaker Jenkin van Zyl, both wearing Charles Jeffrey Loverboy clothing and hats; van Zyl wears Falke socks and his own belts.

Photograph by Tim Walker. Styled by Sara Moonves

As we come to the oval drawing room at the Wallace Collection, Jeffrey stops in front of his favorite Fragonard painting, A Boy as Pierrot, which depicts a child with commedia dell’arte painted cheeks, wearing a theater costume that is too large for him. The peculiar formality and playful charm of the 18th-century portrait de fantaisie creates a fascinating dialogue with the six-foot-four-inch figure with shocking pink hair standing before it. “The past is a different country, and everyone is welcome,” ­Jeffrey says enigmatically, and then smiles.