Gentleman Jim, the Tailor

On the oral histories of a Harlem haberdasher. 

By Magda Lena Griffel

Illustration by Iris Pope

Tweed, silk, single-breasted, double-breasted, pin-striped, paisley, heather, jewel-toned—each day, Gentleman Jim dons a different hand-made waistcoat. Some days, he’ll have a neat little kerchief tied around his neck, and others, a classic epcot tie. My favorite is a blue-and-silver damask number, layered over a white button-down. He tops it off with a red scarf.

He should be this decked out: from 1962 until his retirement, Mr. James E. McFarland (also known as Gentleman Jim) worked as a tailor in Harlem and Atlanta, sewing suits for some of the most prominent Black figures of the mid 20th-century. Since retiring, he’s also become a minor Youtube influencer. He started posting sewing tutorials in 2015, and eventually—by popular demand—biweekly oral histories for his series known as “The Brother from Harlem with the High School Education,” which now has 54 episodes and a more recent six-part spin-off series, “Harlem in Black and White.”

I stumbled upon McFarland’s videos while trying to embroider a waist-coat of my own, a final project for a class on queer Harlem history. His stories are sprawling. They recount his time as the right hand man of preeminent tailor Orie Walls at Orie’s Custom Tailoring, but are also nostalgic vignettes of his childhood and community. Born in Jamaica, McFarland and his family moved all around New York City before settling in Harlem, from where he attended the High School of Fashion Industry, and became a fixture of the neighborhood himself. “There ain’t nothing in Harlem I don’t know about,” McFarland proclaims in one of his videos, flashing a proud grin.

McFarland worked at Orie’s Custom Tailoring from 1962 to ’72. Located on 125th Street next to the Apollo Theater, Orie’s business grew exponentially as the vast majority of the Apollo’s performers came through the store, attracted by precise custom tailoring, new silhouettes, and experimentation in color. With pink, yellow, and purple fabrics imported from London, Orie’s created a signature style. “[I]t became a phenomenon. Everyone wanted one,” McFarland said in a GQ interview. Duke Ellington, Dizzy Gillespie, Jackie Robinson, and Miles Davis came through the store. In one of his videos, McFarland describes Muhammad Ali coming in for a suit and asking McFarland to help get him a woman’s number. Prominent civil rights activists like A. Philip Randolph and Bayard Rustin would get their tailoring done at Orie’s too. No other suits, the fashion designer, haberdasher, and oral historian known as Dapper Dan said, could compare to what Orie Walls was making. If customers couldn’t afford a new custom suit, customers would come in with thrifted ones and get them altered to perfection.

Orie’s suits are a part of a long lineage of Black dandy fashion, a tradition characterized by elegant men’s formal-wear, sharp, custom tailoring, and, most essentially, a gesture towards dignity—of self-definition and self-expression. The concept has been having a resurgence in cultural and academic attention recently, in large part to Monica Miller’s book Slaves to Fashion: Black Dandyism and the Styling of Black Diasporic Identity and the 2025 Met exhibition and Gala it birthed, Superfine: Tailoring Black Style. “Whether a dandy is subtle or spectacular,” Miller, a professor at Barnard, writes in an introduction to Superfine, “we recognize and respect the deliberateness of the dress, the self-conscious display, the reach for tailored perfection, and the sometimes subversive self-expression.”

Tailoring is a deeply meticulous, intentional act. It is a literal creative and industrious process, but it’s also a loving attitude towards memory and storytelling. McFarland wants to tell a complete story, but “I can only give my perspective on what I knew, saw, and read,” he admits. “I’m going to tell what Harlem meant to me.” 

Miller, who sat down with Gentleman Jim and talked about his background and craft while creating Superfine, told me that speaking to him felt like watching one of his videos. He’s a natural-born storyteller with a gentle, steady timbre—as precise in his language as he is in his craft. In his oral histories, he gives every memory equal relevance, as his many tangents become embedded into the greater arc of his story. He is constantly, calmly, confidently insisting that the history of his craft and his neighborhood is vital to any complete understanding of American life. 

“They're not waiting for people to come to them,” Miller said of oral historians like Gentleman Jim and Dapper Dan who are remembering the age of the 125th Street haberdasheries. “They understand the importance of what they have to teach people.”
And they tell these stories, Miller noted, in the absence of the actual material objects. Gentleman Jim doesn’t have any of the suits from the years he was working at Orie’s. Everyday clothing of family members is not typically preserved, and even in the case of more prominent Black figures, their clothing is mostly lost to history. Poring through archives, I couldn’t find a single photo of Orie’s storefront, and only the Amsterdam News, a newspaper by and for Black New Yorkers, published the occasional advertisement enticing readers to come to Orie’s Custom Tailoring and “get your old Double-breasted Suits made into the Latest Single-Breasted Two or Three Button Styles.” What is preserved, the accounts of Black American life—the mundane, the respectable, and the profundity within that—are few and far between, because memory in this country is politicized, racialized, steamrolled for the sake of white-national narrative cohesion. 

McFarland’s entire project undermines that: the validity of “objective” history. His stories, too, are an act of tailoring—precise and, as Miller writes, deliberate. His videos assert that the gesture of storytelling, of sitting down in your homemade waist-coat and gently recalling the past is intellectually worthwhile, and that it is the individuals who lived through these stories who ought to be the arbiters of relevance. His stories sound like fables—not because they are fiction, but because they are fragile, precious, engrossing reconstructions of memory.