Jackets that cover the ass? Hard pass for Terry Singh

When Terry Singh says, “Getting dressed is a sacred ritual,” you know that the 58-year-old means it. His mornings are marked by music—Indian bhajans and Black gospel tunes, to be specific—and the quiet pleasure of rearranging pieces on the bed while his wife Kelli gets ready nearby. He tells me that he dresses the way some people cook: intuitively and with reverence, altering a little here, layering a little there. His thoughtful approach to dressing makes sense when you consider that he’s more interested in reshaping codes than he is in current trends. “I’ll try two, three things [to wear],” he says, “I’ll surprise myself sometimes. That’s the joy.”

The fashion designer has made a name for himself by reimagining menswear through the lens of Indian draping. Given that he taught himself to sew, it’s no small feat that the first show for his eponymous menswear label was held at New York Men’s Day in 2022. That was where the world was first introduced to his signature silhouette—a reimagined tuxedo jacket and white button-down with a wrap-style dhoti instead of the traditional tailored trousers.

Singh spent his formative years in New York’s Hell’s Kitchen in the rough and tumble ’70s and ’80s, a time and place he credits with imparting a grit and toughness that still lingers in his style and continues to give it a masculine, streetwise edge (cue his signature Doc Martens boots). Despite his status as a consummate New Yorker, Singh credits a pilgrimage to India as the turning point in his life and as the moment that coaxed him to leave his decades-long career in publishing and advertising for fashion.

What began as a short trip in 2014 turned into a months-long stay spent meditating with yogis and living in ashrams, a time where he both reclaimed his roots and forged a vision for the future. “I’m Indian, but I had never been to the country. And I just fell in love with being Indian,” says Singh, who is of Guyanese-Indian heritage, explaining that this trip was the first time he ever felt “supported by the land”.

He arrived back in New York a changed man—not just spiritually but also sartorially. “I’d been wearing a lungi or a dhoti everyday,” he explains, “And I didn’t want to go back to wearing pants.” He tried to recreate the look in a way that would fit in with city life—hiring seamstresses and buying high-quality designer fabric—but they just couldn’t see what he was seeing. “They didn’t have the experience I had,” he says, “So, I bought a sewing machine and learned to make the clothes I wanted to wear myself.”

What emerged was a new silhouette—part lungi, part dhoti, part wrap skirt—structured in panels so it didn’t have to be re-draped each time. Singh is partial to pairing his dhotis with cropped jackets or crisp button-downs, and without trying to, he has created a new kind of uniform that pushes the boundaries of what menswear can be. 

“I didn’t even realise it at first, but people were photographing me everywhere I went,” he says. In Milan, a young fashion student stopped him at a bar and said, “This is what I came to Milan for,” gesturing at his outfit. “She was from Florida,” he says of the woman, “I thought, ‘Holy shit.’ They came to Italy to see a New Yorker dressed like me.”

Singh returns to that moment often and thinks of it as the instant he realised that the way he dressed was both personal and public, and that his style had unintentionally become a symbol of permission. “Two young guys came up to me in Fort Greene [Brooklyn] and said, ‘Thank you for being you.’ At first I didn’t know what they meant, but I later realised that seeing me in what they thought was a skirt—a man my age—made them see that there’s a possibility for them to live that freely too. Interestingly, it’s always young people,” he says proudly.

Since then, Singh has begun to think of his style not just as an aesthetic, but as a new dialect in the language of masculinity and menswear. Which is why you’ll see him pair his dhoti wraps with Kobe Bryant jerseys and silver sneakers, or why the cuts of his cropped jackets are all inspired by sleek Italian and Spanish tailoring but religiously matched with chunky combat boots. There’s a tension to his style that invites curiosity, and this subversiveness is what fuels him. “What I was doing,” he says of his style, “was opening up a way for people to engage.”

Inside his closet? Endless white and black dress shirts (Singh believes that basics let you tell a story), vintage basketball jerseys, and Gucci military jackets. Oh, and one souvenir from his previous avatar as an advertising bigwig—a traditional suit that he says he’ll never wear again. “It covers my ass,” he laughs, talking about the suit’s blazer, “Why would I want that?” Singh’s cropped jackets work to elongate the leg, open the body, and shift the gaze, and, of course, do not cover the ass. “I’m 5’8” but I model my own work. It’s all about proportions.”

Courtesy Rose Callahan

In spite of his reputation as an unrepentant rule-breaker, there’s an old-world charm to the way in which Singh thinks about masculinity and menswear. “There are certain rules that I stand by,” he says. “Which is that a man should always be elegant, presentable, and statesman-like. And also open to communication and not be stand-offish.” That’s evident also from his Instagram feed, which is conspicuously devoid of the traditional flatlays and product shots. Instead, there is the warmth of candid, sunlit portraits that speak more to a way of life than they do to a catalogue of style.

A trait Singh shares with designers like Tom Ford and Rei Kawakubo? He wears his own pieces daily, not as an exercise in branding but as a testament to a belief system: that what we wear has the power to reflect who we are, and that style at its best is about access rather than aspiration. “It’s functional,” says Singh, showing me the ease with which he can wrap and unfurl his panelled dhoti, “And easy.”

It might be easy, but that doesn’t get in the way of it also being radical.