Meet Your Favorite Menswear Expert’s Favorite Menswear Experts

Vito Di Maio / Dendera Studios6 min readDo you ever wonder who your favorite menswear experts’ favorite menswear experts are? Talk to anyone with a penchant for classic tailoring mixed with a healthy dose of personal flair, and there’s a very good chance you’ll hear about brothers André and Keith Churchwell. Their fans run the gamut from fashion insiders and editors to writers like G. Bruce Boyer, the author of seminal books like Elegance: A Guide to Quality in Menswear (1985), and Derek Guy, an Esquire contributor who you might know as @DieWorkwear—aka the “Menswear Guy”—on X.“They really know what they're doing,” says Boyer. “A lot of people will say, ‘Oh, well, he's just a guy who looks good in clothing.’ That is never true. A guy who looks good in clothing knows why he looks good in clothing.”The thing is, the Churchwells aren’t fashion guys by trade. The Nashville-born siblings are doctors—two of the most esteemed cardiologists the country, in fact—who were born in the Jim Crow-era South and navigated their way to success despite the myriad obstacles thrown in the path of Black professionals. They’re fluent in good food, good music, good theater. And they just so happen to dress impeccably, which is why they’ve garnered a following of guys looking for an antidote to fleeting trends and unsubstantial influencers.Vito Di Maio / Dendera StudiosKeith (left) and André Churchwell.I met the Churchwells a year ago through the tailor Leonard Logsdail, who has one of the finest sartorial eyes in the industry. He, for his part, met them through Boyer about three decades ago. André had read Elegance and reached out for a tailoring recommendation. Boyer made the connection, Keith was soon brought into the fold, and all remain friends to this day.Over the last few months, I’ve spent hours chatting with Keith and André about their upbringing, their dress sense, and their outlook on life. What I’ve learned amounts to so much more than lapel width or shoe choices (though those do matter). Ultimately, it’s about the appreciation of craft, the cultivation of taste, and the art of becoming the best version of oneself.The Churchwell Way There’s one thing the Churchwells’ father, Robert, would say every time his young sons walked out the door of their home on North 9th Street, André tells me over Zoom: “’You’re representing the family.’ Everything derives from that. Being Black, in East Nashville, of all the things we learned, that is what was deeply inculcated into our bones, into our hippocampi. The big stone in the ocean, the thing we stood on every day as kids or young men: You’re representing the family.”We’re joined by Keith—he’s calling in from his home in Connecticut, André from his office in Nashville—who remembers how that translated to things like seeing his first movie, Bambi, in a coat and tie. And then, of course, there was church on Sunday.Vito Di Maio / Dendera Studios“The big stone in the ocean, the thing we stood on every day as kids or young men: You’re representing the family.”“It’s important to note the importance of the Black church and the history of it in Black America as a place where we could come, be ourselves, and develop our own sense of style,” says André. “We weren’t under the thumb of the man on those Sundays, those treasured Sundays. And so those guys, man, they would come and it would be a dress off.”On those Sunday mornings, André, Keith, and the rest of the Churchwell children bore witness to style lessons that would set them on a path for the rest of their lives. “He didn’t have a salary that allowed him to do bespoke,” André says of his father, who was the first Black journalist to work as a full-time reporter for a Southern newspaper. “But one of the great lessons we learned from him and others of his generation was that you don’t have to be bespoke to be really clean.”Vito Di Maio / Dendera Studios“Get yourself a good tailor!” Keith implores. “No matter what.”Case in point: a white suit, snagged for a bargain from Filene’s Basement and thoroughly altered, that André wore to a celebration before his graduation from Harvard Medical School. Keith was there, and recalls his brother standing out for all the right reasons amidst a sea of navy blazers. “I have no idea how he did it,” Keith says, “because he had no money!”With Surgical Precision “If you ask André how wide his lapel is, he'll be able to tell you within a quarter of an inch without even thinking,” says Boyer. “And we know it's not going to cure a lot of the world's problems, but it is important because it shows what we think of ourselves and we want to project that to other people.” Finding that balance means walking a fine line–knowing the value of dressing well without letting it become a vanity project or an expression of ego, a principle that the Churchwell’s exemplify. “How many men can you point to who are somewhat public who are good role models today?” Boyer asks.It’s a topic Keith and André brought up time and again in our conversations: the lasting impact of their father and mother, Mary Elizabeth Buckingham Churchwell, whose own enviable styles made their mark alongside figures like Fred Astaire, Cary Grant, and Gary Cooper. “Now, you don't have Robert Churchwell Sr. types—fathers sitting down discussing with their sons the appropriate type of tie, shirt, jacket, and so forth,” says André. “Kids want to know more; you can tell these young Black guys want to know how to dress. The problem is they've not had any models and they're struggling out there.”Vito Di Maio / Dendera Studios“Kids want to know more; you can tell these young Black guys want to know how to dress,” André says. “The problem is they’ve not had any models and they’re struggling out there.”André and Keith are only too happy to be the people those young men come to for advice. André tells me he attended the funeral for a friend and patient recently. “His son came up to me and asked, ‘Dr. Churchwell, does this look okay?’ and I told him he had done spectacularly. It’s about presence. You want people to feel like they can talk to you.”When it comes to the specifics of building a wardrobe, both brothers advocate for the classics: a navy suit, a white button-down, gray worsted trousers. “And get yourself a good tailor!” Keith implores. “No matter what.” (It’s no surprise, then, that both André and Keith are regular customers of beloved bespoke suit maker Leonard Logsdail.)Playing JazzThe Churchwells are, of course, well beyond the basics; in the time that I’ve known them I can’t recall ever seeing an outfit twice. On every one of our calls they are impeccably styled—colorful suits with silk cravats, double-breasted jackets that move like water as they speak, and elegant touches like a cygnet pinky ring. Clothes, they tell me, are about self-expression, and the sense of joy and pride they take in what they wear is obvious.It is Boyer who André calls his “post-doctoral” advisor in style, introducing him to all the best tailors, shirtmakers, and haberdasheries. But dressing with the Churchwells’ level of flair is something of an art form–a skill that is earned.Vito Di Maio / Dendera Studios“Style is not for sale in the shop window. It’s something you have to think about and experiment with. It’s a process,” Boyer says. “I tend to navigate towards guys who have style and taste, and I think Keith and André are good examples of that.”“Personal dressing is like playing jazz,” André says. “You learn all the rhythms, you learn the scales, you learn all the rules, and then you learn to break them based on your own interests and your own sensibilities.” Keith chimes in: “You can do all that and not look like a clown show because you’re at that higher level of dress.”The point, according to the brothers, is to look both impeccable and effortless. “You don’t want to look so studied that people can detect you were in the mirror for an hour,” says André.It’s something that experts like Boyer can really appreciate, and the reason that the menswear cognoscenti have embraced the Churchwells even in an era when casual clothing has replaced the suit and tie as the daily uniform.“Style is not for sale in the shop window. It's something you have to think about and experiment with. It’s a process,” Boyer tells me. “I tend to navigate towards guys who have style and taste, and I think Keith and André are good examples of that.”He continues: “It's so unfair. Because they know almost as much about clothing as I do and I don't know anything about cardiology!”