Men's Lifestyle May 7, 2026 0 Comments

Unlocking the Secrets Behind the Country’s Best Tailor: What Makes Their Craft Unstoppable and Irresistible?

Ever wonder what it takes for a master tailor to remain at the peak of his craft for nearly half a century? I found myself asking this as I delved into the story of Leonard Logsdail—a man whose name is whispered with reverence among costume designers and style icons alike. Imagine being the go-to guy for not just the best costume wizards behind shows like Succession, but also for the finest dressed men on the planet. That’s Leonard. At 75, while most consider slowing down, Leonard is not just moving shops but embarking on a new chapter—two blocks from Grand Central, yet still a towering figure in bespoke tailoring. What’s the secret sauce behind a career that blends old-world Savile Row precision with a distinctly New York hustle? Let me tell you, it’s a mix of passion, integrity, and a wicked sense of humor that disarms even the most jittery newbie in menswear—like me, back when I first called him. Stick around—there’s a lot to learn from a man who doesn’t just make suits but builds trust stitch by stitch. LEARN MORE

8 min read

When I first met Leonard Logsdail, I was deep in the costume design beat, writing about the often under-appreciated world of storytelling through clothes. Everyone I spoke with was top of their craft, costuming for shows like Succession, or working as longtime collaborators of Martin Scorsese. And everyone I met had one go-to guy for suits: Leonard Logsdail.

Being the suiting wonk that I am, my interest was piqued, but the more I learned about Leonard, the more intimidated I became. Calling Leonard the go-to guy for the best costume designers in the business was, as it turned out, an understatement. Leonard, I would learn, is the go-to tailor for some of the world’s best dressed men. When I had the chance to talk to him, I was still relatively young in the menswear world, and he would be the first Savile Row tailor I met. I was a mess with nerves. But as soon as we got on the phone, I was disarmed. He was warm, funny, down to earth. Confident and assured in his work, to be sure, but without the arrogance or insular disposition I expected of someone with his reputation.

Now, at 75, Leonard is embarking on a new adventure—moving his shop from the Midtown spot where he’d been for almost 30 years to a new space, two blocks from Grand Central Station. His address may be changing, but Leonard remains a singular force in the industry.

Tailor working on fabric with scissors and measuring tape.

Lucas Goldman / Dendera Studios

Logsdail cutting fabric in his Manhattan workspace.

“A Class All His Own”

The son of a milkman, Leonard grew up in London in a home with no indoor plumbing. He started tailoring school when he was 15, at his sister’s suggestion, something he’s told me was a divergence from the norm of where he grew up. Trade schools were a typical path for young men his age but it was more common to enroll as brick layers than tailors. For Leonard, it was kismet—immediately, he could intuit the shapes, how the fabric needed to be cut. After graduating, he became the youngest tailor to hang a shingle on Savile Row where he stayed for two decades serving clients from all over Europe.

Then he fell in love with an American girl—his wife Barbara—and the two set down roots here in the U.S. Today, the couple lives in Connecticut where they have raised their family. Leonard commutes into the city everyday, unless he’s not on the road for clients or trade shows.

When I called Leonard, he was entering hour seven of a two-day drive to Georgia, where he was presenting his wares at the Dallas Safari Convention. In addition to the best bespoke suits money can buy, Leonard specializes in luxury hunt clothing. Gorgeous, earthy tweeds adorn custom hunting jackets and britches, and he tells me he’s even made matching gear for his hunting clients’ dogs on occasion. (When I spoke with Michelle Matland about her work on Succession, she remarked that when it came to outfitting characters for the hunt episode, Leonard needed no instruction; he knew that world inside out and created perfectly styled garments.)

Tailoring workshop with two people working on garments.

Lucas Goldman / Dendera Studios

“He’s in a class all his own,” said the creative director of a Savile Row tailoring house. “He’s a master tailor.”

Leonard started working with hunt clients when Hudson Farm, a private club in New Jersey, was in need of a new English tailor to look after its clients. The club’s director was set to travel to London to scout a new tailor. That’s when a friend of Leonard’s who was, at the time, the American director of Barbour, said “Why do you need to go over there? We’ve got a Savile Row tailor right here in New York: Leonard Logsdail.”

“We just hit it off,” Leonard tells me. Today, Leonard says some of his best bespoke clients come from that world. They meet Leonard because they need tweeds to go with their rifles—which can go for $150,000 a piece—and soon realize they can have their suits made by Leonard as well. Call it one-stop shopping for the über wealthy.

In the time that I’ve known Leonard, I’ve heard some version of this claim easily a dozen times: There’s a need for a bespoke suit, an expert to handle a challenging costume design job, a complicated tailoring request, and inevitably, someone puts Leonard’s name forward. I remember interviewing the creative director of an historic tailoring house on Savile Row and mentioning Leonard’s name in passing: “Leonard,” he said with immediate reverence, “He’s in a class all his own. He’s a master tailor.” And it’s true: A Leonard Logsdail suit is as close as you can get to perfection.

Man dressed in formal attire with a scarf standing in a hallway.

Lucas Goldman / Dendera Studios

“I think very highly of Lenny,” says menswear writer and expert Bruce Boyer, “he is the best tailor in the country.”

Menswear expert and journalist Bruce Boyer tells me Leonard is, in his estimation, the finest bespoke tailor in the country. “He’s a true bench-made tailor,” he tells me. “He can make his own patterns, his work is done in his shop, by hand. He’s one of the few tailors in New York who is doing full custom; every buttonhole is done by hand. I think very highly of Lenny—he is the best tailor in the country.” Of Lenoard’s house style, Boyer points out that it meets a unique aesthetic demand; having come from Savile Row to an Ivy-obsessed America, Logsdail created the perfect amalgamation of the two. “The Brits were making what I call a very hard garment, it was very architectural. And Americans were still more into Ivy League clothing–soft shoulders, not much in the chest piece,” he explains. “And Len looked at that and understood it. He does the best of both worlds.”

But Leonard is not just an exceptional technician. It’s his bedside manner, so to speak, that keeps clients—A-list celebrities, titans of industry and politics, and royalty among them—coming back for more.

Three men in formal attire posing together in a luxurious hallway.

Vito Di Maio / Dendera Studios

Logsdail with two of his clients—brothers, doctors, and menswear aficionados Andre and Keith Churchwell—at the Waldorf Astoria in New York City.

All in Good Fun

In addition to impeccable tailoring, Boyer says that Lenoard’s disposition is a selling point all its own in his business. “He’s witty and he has a great sense of satire and sarcasm,” he tells me.

“Just because I’m doing well and I’m well known, doesn’t mean you become arrogant or dismissive of people,” Leonard tells me. “I always say, ‘I take my job seriously, I do not take myself seriously.’ I’m always looking to have some fun.” Honesty is the foundation of the relationship between Leonard and his clients. For all its technical demands, the tailor-client dynamic is as important to nurture.

“Ninety percent of the business is psychology, 10 percent is tailoring,” he says.

It’s an often vulnerable relationship, and tailors are notoriously privy to their clients’ personal lives, not unlike a therapist. “Well they’re standing there in their underwear!” Leonard laughs. It’s why he always encourages people to do their research before committing to a tailor. “I always ask, have you been around to see other tailors? It’s very important, because when you make that final decision you’ve got to be happy with it.”

Tailoring process with scissors and measuring tape.

Lucas Goldman / Dendera Studios

Close up on Logsdail’s cutting, which is revered by fellow tailors.

Leonard prides himself on his honesty; he’s not one to mince words about what he thinks does or doesn’t work. “I always say, ‘Look, I’ve got a big mouth and you’re going to get an opinion from me. You don’t have to take it, but you have to hear me out because I don’t want you to come back and say that I should have told you I didn’t like the fabric!’” he says. “If you want me to make something I don’t like, I’ll always be okay with that, but I will tell you my opinion. It’s a level of honesty—it’s not about the sale, it’s about building trust.”

Beyond aesthetic and design, Leonard’s integrity is bar none. I’ve had the pleasure of meeting some of his clients over the years and each one of them counts themselves lucky to be wearing a Logsdail suit. They know they can trust him to make them look good, and to take care of them; he won’t sell a client on a fabric or an idea just because it comes with a shiny price tag. He tells me about a particular wool he carries that would tip the cost of an overcoat just shy of $40k. “I’ll pull out a cashmere that [costs half as much] and ask them if they can see the difference.” If they still want to pay the heftier price tag, Leonard is happy to indulge them but not without making sure they have all the information they need.

The same practicality applies to special-occasion dressing. If money is no object, he says, go for it: get the stylized cut, get the wide peak lapel, get the seasonal fabric or color. But a bespoke suit is an investment, one he believes should last. “[I see it with] weddings in particular, they’ll talk about a fancy design,” he says. “And I’ll ask them: ‘So do you see yourself wearing this afterward?’ If they want to wear it afterwards, they need to think before moving forward. It’s my job to make sure they know what they’re doing.”

Two individuals posing together in a grand interior space.

Vito Di Maio / Dendera Studios

Logsdail with his wife, Barbara, at the Waldorf Astoria.

A Family Man

It’s been six years since our first phone call and Leonard remains my North Star for all things menswear. And over the years, I’ve been lucky enough to glean Leonard’s wisdom not only about suiting but about life. Ask Leonard why he does what he does, and his answer is always: “My job is to provide for my family.” But how much Leonard truly loves what he does is evident too, and he feels lucky that he’s able to provide for his family doing something he’s so incredibly passionate about.

“It wasn’t always like that,” he says of his ability to balance work and family. “I used to work 60, 70, 80 hours a week building my business up.” After he and Barbara married, he cut down on his hours and quickly found that even though he wasn’t traveling as much as he had in the past, business was steady and he was able to focus more. “It keeps me on the straight and narrow,” he says of always keeping his family as his top priority. The pride Leonard takes in his family is the throughline in almost all our conversations. When discussing the sterling reputation he’s earned, he’s quick to pivot to the ways it’s helped his children achieve their goals. He talks proudly about seeing his son open car doors and walk on the street side of the sidewalk, gentlemanly etiquette Leonard has taught him by example. He gushes about his daughter’s knack for style, something he insists she gets from her mother.

Tailor demonstrating measurement technique.

Lucas Goldman / Dendera Studios

“I may be 75,” Logsdail says, “but I’ve got more energy than most 50 year olds and I still have a passion for my business.”

And when it came time for Leonard to decide to move into a new space, it was Barbara’s trusted counsel that pointed him in the right direction. “I hit 75 and everyone was saying ‘You should take it easy! You worked hard enough!’ But looking back, I think it was a bit of a transfer of feelings.” At first, Leonard contemplated a space in Connecticut, closer to his home. But it didn’t feel quite right. “Barbara didn’t want it; she didn’t see it as a step forward.” Then his real estate agent called him with a sixth-floor penthouse in Manhattan and it clicked. Within days he had signed a five-year lease with a five-year option after that. “Barbara was right,” he says. “I’m truly blessed with someone that cares for me. And I may be 75, but I’ve got more energy than most 50 year olds and I still have a passion for my business.”

With the move to his new space well underway, Leonard is poised to be the second notable resident at 29 West 46th street. “It’s where Irving Berlin used to live,” he tells me.