From his first whimsical sketches, Marc Jacobs’s pencil has intuitively tapped the zeitgeist. In 1984, when he was still a design student, his oversize polka-dot sweaters swept up a batch of awards at Parsons School of Design. Within days, the Manhattan boutique Charivari had commissioned a set, and shortly after the ink dried on Jacobs’s diploma, he was offered his own label.

But as the saying goes, nothing good ever comes easy. The next few years would test Jacobs in many ways. In 1992, he was gaining a toehold as the new head of the classic sportswear label Perry Ellis when he staged his infamous Grunge show. While many in the front row adored his upmarket take on garage-band chic—modeled with just the right slacker insouciance by Shalom Harlow and Christy Turlington—his bosses, who promptly gave him the boot, did not.

Jacobs’s streetwise aesthetic—in his words, “a little preppy, a little grungy, a little couture”—won him the hearts of hip chicks the world over, including Sofia Coppola, Winona Ryder, and Kate Moss. For 30 years, he has been building his brand of playful clothes and accessories.

In 1997, the French conglomerate LVMH tapped the native New Yorker to jazz up the then-143-year-old house of Louis Vuitton. He gambled Vuitton’s fortunes on collaborations with ’80s neon designer Stephen Sprouse and the whimsical Japanese artist Takashi Murakami, and the results (subverting the L.V. monogram into graffiti scribbles and Skittles rainbow colors) were solid gold. Within 10 years, Jacobs had quadrupled the company’s profits. By the time he bid it adieu in 2013—to focus, reports said, on taking his own label public—Vuitton was firmly entrenched as one of the most desirable brands in the world.

Back home in New York, Jacobs’s irreverent wit prevails. His models might style their hair in enormous poodle-poufed Afro wigs, or they might wear Eisenhower-era cocktail dresses with a hot pink fishnet-stocking print, or they could be swagged in Folies Bergère–gone–punk plumage and chains (as at his curtain-closing Vuitton show in October 2013). “Go out on the street—that’s how a stylish girl dresses,” Jacobs once said. “Fashion has to have irony right now.”