The men’s fashion market has never been more crowded. Social media has turned getting dressed into a competitive sport, and countless new labels have launched in the past decade, each fighting for attention in a space where trends change overnight. Standing out is no easy feat—yet Terry Singh has managed to do just that with one bold move: putting men in skirts.

Before he began reimagining menswear, Singh was the quintessential corporate professional: suit-clad, tie-knotted, navigating the world of advertising and publishing. His first brush with fashion came in the boardrooms of corporate America, where top executives commanded attention in $4,000 suits and Italian loafers. Singh followed suit, literally, embracing the sharp Armani aesthetic of the ’90s.

But eventually, the uniform lost its appeal. Singh began experimenting with bolder tailoring, electric-blue suits, and patterned shirts until, on his 50th birthday, he hit a breaking point. The rigidity of corporate style no longer fit the life he wanted. He walked away and decided to start his own fashion line.

That decision led him to India, where everything changed. “I started wearing a dhoti,” Singh recalls, referencing the draped wrap worn by men for centuries. “At weddings, I’d see men in these elegant white cloths edged in gold, and it made me rethink everything I believed about masculinity. I realized that equating suits with masculinity is a Western concept, and that my own style had been shaped by a colonial mindset.”

Back in New York, Singh tried to adapt dhotis into his wardrobe, buying fine fabrics online and draping them himself. But they never held up. So he hired a seamstress, then a designer, and eventually bought his own sewing machine and began experimenting. His first breakthrough came in the form of a pleated wrap.

“The pleated wraps gave me the freedom I was searching for,” Singh says. “Ten years ago, I’d walk out the door, and street style photographers would swarm. Suddenly, I was everywhere on Instagram.”

Encouraged, Singh traveled to Italy to source fabrics. A chance encounter with a model pointed him toward Pitti Uomo, the world’s most influential menswear trade show. Denied entry at first, Singh improvised: he hired a photographer, staged shoots around Florence, and leveraged those images into a coveted pass. The gamble paid off, and Singh not only became a street-style sensation but also met a manufacturer who produced his first samples. Then COVID hit, halting his momentum.

When the industry reopened, Singh quickly reestablished himself. Fashion Group International spotlighted his work, leading to multiple seasons at New York Men’s Day, the NYFW showcase for rising menswear designers. There, he caught the eyes of editors, stylists, and buyers, all intrigued by his fearless approach.

Critics told him men’s skirts would never sell. Singh ignored them. Today, he has a growing base of young customers eager to push the boundaries of style. “Change is slow,” he admits, “but I’m not chasing change. I’m creating freedom. This militaristic, buttoned-up idea of menswear—that’s what I’m rejecting.”

Next on his agenda: a limited-edition drop of his “Essential Wrap,” a piece Singh believes could become as fundamental to the modern man’s wardrobe as a blazer or pair of jeans. His mission is clear, and his message even clearer: Terry Singh is changing the world one skirt at a time.