The Black Tailors Who’ve Kept Dandyism Alive for Decades ( Birm, Chi, Det)

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The Black Tailors Who’ve Kept Dandyism Alive for Decades​

April 25, 2025

From the barbershop-lined blocks of Birmingham, Alabama, to the storied storefronts on Chicago’s West Side, Black-owned tailor shops have long stood as quiet custodians of cultural memory. These mom-and-pop ateliers—many in operation for decades—are more than places to hem a pair of trousers or tailor a jacket; they are institutions of tradition, skill, and, most importantly, community. Black tailoring, as both a craft and a calling, has dressed generations—for Sunday service and first jobs, protest marches, and graduation stages. Through the decades, these tailors have stitched not only fabric but legacy.

As we approach the opening of The Metropolitan Museum of Art’s Costume Institute exhibition Superfine: Tailoring Black Style and the 2025 Met Gala—inspired by the work of scholar Monica L. Miller and her seminal text Slaves to Fashion: Black Dandyism and the Styling of Black Diasporic Identity—there is no better moment to honor the artisans behind the seams: the Black tailors who’ve dressed generations of Black communities for movements, milestones, and everyday moments

Tailoring within Black communities is a tradition forged through resistance, care, and skill—and one that traces back to the era of slavery. In Slaves to Fashion, scholar Monica L. Miller explores how enslaved individuals reimagined their issued garments to express individuality and autonomy. They adorned them with salvaged fabric or ribbon, “borrowed” fine clothing from enslavers for special occasions, and created underground clothing economies that allowed them to either enhance their appearance or pass as free. These early acts of sartorial subversion laid the foundation for Black tailoring as we know it today, both a craft and cultural statement.

Black folks have long wielded style, using dress as a tool of survival, pride, and radical self-definition. Across the country—in cities like Detroit, Chicago, and Birmingham—the tailor’s shop has remained central to that evolution.
Ahead, Vogue visits the shops and studios of master Black tailors across the country for their reflections on what it means to preserve tradition, push the craft forward, and keep the legacy of Black tailoring—and dandyism—alive and well

 

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Robert Hill: Robert Hill Custom Tailors, Birmingham​

In Birmingham, Robert Hill has been a stalwart figure in Black tailoring for over four decades. Since opening Robert Hill Custom Tailors in 1983, his shop has become a trusted institution in the city’s Black community, dressing generations of men for church, Easter Sundays, weddings, and milestone celebrations. “My parents made sure we went to church, and that’s when I first started loving suits,” Hill tells Vogue. His journey into tailoring began from necessity—“I’m a short person with a small waist and couldn’t find clothes to fit me,” he says—but quickly turned into a lifelong craft, honed through training with master tailors in the early 1960s. Today, Hill’s signature lies in precision and patience. “A good suit starts with quality fabric and workmanship,” he says, a standard that’s remained unchanged even as trends come and go. During economic downturns, when many shops shuttered, Hill’s focus on alterations kept him afloat: “People didn’t buy new—they brought in what they had. That’s what kept me in business.”

Photo: Courtesy of Robert Hill Custom Tailors

Beyond the sewing machine, Hill’s work represents a quiet preservation of Black elegance and self-presentation in the South. His tailoring speaks to a form of dignity rooted not only in fit and cut but in care. “Tailoring is a lost art,” he reflects. “Young people don’t have the patience. It takes time to learn this.” Hill estimates that 75 to 80% of his business comes from alterations, but he still offers custom suiting, parsing through fabric swatches and style books and adjusting patterns, designs, and fit for each client. In a field with few successors, Hill holds fast to the values of tradition, discipline, and legacy. “This kind of work, it teaches you to slow down, to be patient,” he says. Though fast fashion and fleeting trends make up much of today’s fashion landscape, Hill remains committed to a slower, sharper vision.

 

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Tony Stovall and Cliff Green: Hot Sam’s Detroit, Detroit​

Photo: Andre Terrell McWilliams

In Detroit, the legacy of Black dandyism lives on through Hot Sam’s, the city’s oldest Black-owned menswear store and a cornerstone of the community for over 100 years. At the helm are Cliff Green and Tony Stovall, two old-school clothiers who have owned and operated the downtown Detroit institution for 31 years. The sartorial duo sees tailoring not just as a trade but as a calling. “We’re more than just salesmen, we’re mentors,” Green tells Vogue. He’s been sewing since 1967 and views every alteration as “a form of surgery.” A master tailor by training, Green began his craft in high school after being captivated by the sight of young Black boys hunched over sewing machines, threading their futures through fabric. “It hit me right then—I had to take that tailoring class,” he recalls. What makes a great suit? “The fabric and the inner workings,” he says. “And detail—that’s what separates a garment from being just good to truly exceptional.” For Green, tailoring is more than a technical skill; it’s a practice in precision, care, and cultural memory. “When I sew, I’m thinking about how it should move, how it should fit, how it should feel on the man. It has to mean something.” He’s dressed generations of Black men for weddings, proms, homegoings, and first jobs, all while instilling values of pride, respect, and presence. “It’s not just about the suit,” he adds. “We teach them how to stand tall, how to shake a man’s hand, and how to carry themselves.”

Photo: Andre Terrell McWilliams

For Tony Stovall, Hot Sam’s is a sanctuary for Black men where style meets purpose. “I bought the store so young Black men could see themselves in ownership,” Stovall says. “We all have value, but so often we’re not told that. I wanted this place to say it loud.” His journey started as a teenager, when his father—sharp, cool, and tall—brought him to Hot Sam’s for his first real suit. That rite of passage shaped him, and today he’s passing it on. At Hot Sam’s, getting suited is never just about fabric or fit; it’s a lesson in confidence, care, and self-respect. “We talk about more than clothes,” Stovall says of his exchanges with clients. “We ask about their GPA, their plans, their health. We pour into them.” A prostate-cancer survivor, Stovall uses the store as a space to talk about what Black men carry and what they need. “This is where Black men come to be seen, heard, and styled. We’re not just dressing them for the moment—we’re dressing them for the world.”

Photo: Andre Terrell McWilliams

 

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Joseph Caldwell: TailoRite Cleaners, Chicago​

Photo: Courtesy of TailoRite Cleaners
On Chicago’s South Side, TailoRite Cleaners has been a lifeline for the city’s Black community for nearly seven decades. Opened in 1956 by Korean War veteran Joseph Caldwell, the business was born out of both necessity and vision. “I came back from overseas with no real marketable skills,” Caldwell tells Vogue. “Trades were highly recommended, and tailoring just spoke to me.” He enrolled in an 18-month program through the GI Bill and opened the shop with fellow veterans—Black men determined to create something of their own in a city where few opportunities existed for them. While custom suiting was the initial focus, the reality of serving Black Chicagoans—many of whom needed expert repairs more than expensive made-to-measure pieces—reshaped the mission. “We realized fast that most folks weren’t buying $500 suits, but they needed a zipper replaced or a hem taken up. That’s how we stayed in business.” What made TailoRite thrive wasn’t just skill; it was community. When major banks refused them capital, it was Chicago’s Black-owned Seaway Bank that stepped in. “They believed in us,” Caldwell says. “And our customers did too.”

Photo: Courtesy of TailoRite Cleaners

Now, at 92, Caldwell still comes into the shop, working alongside his family to carry on the craft. “We love our people, and they’ve been good to us,” he says. “It just doesn’t make sense for you to throw away a $1,000 suit when it can be altered to fit you again.” Caldwell moved his shop to its current location in 1987, against the advice of many who doubted investing in a Black neighborhood. “But I believed in us,” he says. “And they’ve continued to show up.” TailoRite is proof that when Black communities invest in their own, style and tradition don’t just survive—they thrive.

 

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Betty Grimes: Betty’s Alterations & Tuxedo, St. Louis​

Photo: Courtesy of Betty’s Alterations & Tuxedo

In a storefront off a quiet avenue in St. Louis, 75-year-old Betty Grimes has spent the past 21 years continuing the tradition of altering and repairing. “I never advertised—people just came,” she says of Betty’s Alterations & Tuxedo, her tucked-away alteration shop. Grimes began honing her skills at 21, sewing hems for customers at her godfather Roszell Johnson’s menswear store, Roszell’s—one of the city’s first Black-owned shops. Decades later, she still uses the same sewing machine from those early days. “I just want people to look better and their best,” she says of her work, “especially our Black men.” With an eye for precision, she adjusts sleeves and hems with the same care she uses to instill self-respect and confidence in her clients.

Photo: Courtesy of Betty’s Alterations & Tuxedo

Grimes’s work has dressed entire generations: promgoers, groomsmen, Delta Sigma Theta cotillion escorts, and even her own grandsons, both of whom went on to college—and to job interviews—in suits she taught them to wear with pride. “There’s nothing I could have bought more important than that,” she says, adding that owning her shop helped her put her grandchildren through college. “That’s why I never really retired.” Grimes is among a shrinking number of Black tailors preserving the nuanced craftsmanship and culture of dressing well. It’s a calling she takes immense pride in. “When I say I open at 9, I’m here at 9,” she says. “That’s what I learned from my godfather. Especially in Black business—be on time, do it right.” In her hands, every alteration is an act of care—a continuation of Black sartorial tradition and a subtle resistance to being forgotten.

 

[Neuromancer]

Does Dapper Dan count ?

 

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Does Dapper Dan count ?

He was front and center at the Met Life event. And they featured an outfit he made for Jam Master Jay in the exhibit.

I think pre-crack era, he might have done traditional suit design and tailoring.

 

[Piff Perkins]

Oh man I can't wait to read this. I like bespoke suits a lot.

 

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@Neuromancer

Spoiler

Rest in Peace to Jay

 

[Ol’Otis]

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