This New York Styling Legend’s Closet Has Jackets Made on Savile Row and Cufflinks From Chanel

It’s a peculiar assignment to dissect the ensembles of legendary stylist Freddie Leiba. From the waist up, it’s all business. He dons a velvet blazer, a button-down, a striped vest, and a tie. Matter-of-fact. Sans frills. His bottom half exudes a different energy. There’s a pair of jeans slung with a chain and cinched with a studded belt. The denim bunches over a pair of Dr. Martens—which he pronounces in full, “Doctor Martens.” He has discarded a newsboy cap that now rests on the table instead of atop his head. Oh, and the cufflinks are Chanel—they were a gift from “Karl.”

This is merely one iteration of a uniform years in the making. The jeans are always vintage Levi’s. The shirts he has tailored to his liking. The jackets he alternates amongst a collection that ranges from an original Tom Ford herringbone to Savile Row tweed. The vest is optional—though the colorful one Yves Saint Laurent gifted him on a holiday trip to Morocco made a compelling case today. Earlier, we had discussed the legendary fashion shows of comrades similar in stature to Saint Laurent, which he had the privilege of attending—McQueen, Jean Paul Gaultier, Chanel—decades prior. There, everyone “dressed to the nines.” What did he wear? Leiba gestured to the garments draped upon his own silhouette. “This,” he shrugged.

The stylist’s name might not be one you recognize, but his work, you would. Born to a seamstress mother in Trinidad, Leiba enjoys the space behind the camera, much more than he does in front of it. His resume includes stints in Interview, Instyle, and Harper’s BAZAAR, French and Italian Vogue. To clear things up, Leiba takes me down the historical rabbit hole, scrolling through his slowly cultivated Instagram portfolio. “So that was Meryl Streep, I worked with her,” he notes, of a photo he styled. “There's Madonna. I put her in a gold suit,” with a rather familiar-looking conical bra courtesy of Mr. Pearl for Jean Paul Gaultier (the former he counts as a friend). “You know who she is, right?” he asks, pausing on an Essence photo of Viola Davis. I laugh, “Yes, Freddie.” He continues, “I gave her her first cover,” then scrolls through images of Isabella Rosslini, Beyoncé, and more.

“I'm walking into a room where you're trying to sell yourself,” he says of his approach to dressing himself throughout his career. “The first thing they see is you. So, I try to look like a gentleman. And then I speak about the purpose of what I do,” he explains. Now is the time in his career where some element of giving back must pair with creativity. Whether that’s donating the proceeds of a photography book that celebrates women to charity or designing a plate to raise money for AIDS research. Early on, he was more focused on wedging his Doctor Martens in the door. “It's not about boasting and showing off; it's about knowledge,” Leiba continues of his approach to styling. “I sell myself with books and conversations.”

His home displays the spoils of his tenure. I nearly trip over what seems little more than a shard of cement, but of course, it’s actually a piece of the Berlin Wall. Leiba was one of the first to step over it after it came down in 1989 with the late photographer Rico Puhlmann. If books equated gold, he’d be a rich man. Fashion, art, and architecture tomes litter the floor in haphazard stacks. Literature has claimed his backroom, lining the built-in shelves alongside old-school physical portfolios. But I think he’d still prefer the books.