In New York, people generally end up with the real estate they deserve. Creative directors of dubious talent settle in over-renovated Tribeca lofts, bankers form rookeries in glass apartment towers that look just like their offices, solitary artists hoard good light in their vast studios, and cash-strapped eccentrics button themselves into improbably nice apartments with huge terraces overlooking the park, causing all who visit to ask, How on earth did you find this place? (What they really mean to ask is: How can you afford to live here?)

Whether this is the result of self-determination or New York’s unfailing hand of fate is one of the city’s great mysteries. Regardless, you can tell a lot about a person from where he or she spends their days. And that’s how one begins to understand that Paolo Martorano isn’t just a tailor but a seriously good tailor, of the variety you’d find on Savile Row, in London, or down some ancient Neapolitan street. In such places, florescent light and the sour smell of freshly steamed wool—telltale signs of the trade—are presumed but well hidden.

Inside the Martorano showroom.

Entering 130 West 57th Street, where Martorano’s showroom is located, is like walking into a building that doesn’t exist anymore. It makes you feel like a chimney sweep in a neighborhood of robber barons. The brightwork is polished to a mirror shine, the terra-cotta-and-marble floor would pass a white-glove test, and opposite the doorman’s desk is a mural that was salvaged from the Russian Tea Room’s old location, across the street.

Near the lobby elevator, framed letters and photographs memorialize the property’s ghosts, from an age when it housed studios and residences for artists, writers, and other bohemian types: William Dean Howells, Childe Hassam, Joseph Heller, José Ferrer, and, later, Tony Bennett, Ray Charles, the Rolling Stones, and Woody Allen.

Martorano, who is just 32, found the space in 2017, when he was starting his own bespoke shop. Hailing from a long line of tailors—his grandfather and his great-grandfather were in the business—he grew up interrogating the seamstress at the custom-clothing shop in his Long Island hometown about the basting marks on a jacket in the store’s window.

Martorano’s building, on Manhattan’s West 57th Street, once housed Ray Charles.

By 2007, he was working for Alan Flusser, the author and men’s-clothing designer who personified the 1980s New York power-dressing look by making Michael Douglas’s suits for Wall Street. “I watched [the film] after buying Flusser’s book Dressing the Man, when I was about 16. At 17, I reached out to Alan, and it led to my first job, which started the day after I graduated from high school,” Martorano says.

He then worked at Paul Stuart and then as the director of bespoke at Dunhill. Along the way, he absorbed everything he could about the history of men’s wear. The showroom is decorated with old Apparel Arts drawings and esoteric tailoring handbooks that detail how to sew a lapel so it rolls properly, which toe the crease in your trousers should point to, and how to press a garment with an iron to shape it and lock the construction into place.

He can explain how, in pre-Castro Cuba, different shades of white and cream linen signified the social class you belonged to, and he swears that linen isn’t the right fabric to wear in Miami. “There’s no time for the humidity to come out of the garment, and it’s never going to be able to be pressed properly.” Doupioni—a light, crisp, slubbed silk—is much better.

Despite his deep grounding in history, Martorano says, “I hate vintage or anachronistic clothing. I don’t think there is anything attractive for a man to look like he just stepped out of a period piece.” His aim is for his customer to be taken seriously and not look like the clothes are wearing him.

George Hamilton in a bespoke suit by Martorano.

It’s precisely this sort of specialized knowledge and passion that has earned Martorano the allegiances of men such as actor Brian Cox, jazz musician John Pizzarelli, and sugar king Pepe Fanjul. His biggest fan, though, might be the debonair actor George Hamilton.

“Paolo’s knowledge of detail … it’s a lost art. People don’t know it,” Hamilton says. The two have a shared vernacular that extends beyond the clothes themselves and encompasses a whole world of stylistic references, from films and photographs to long-dead clotheshorses. Names like Porfirio Rubirosa, Adolphe Menjou, Gianni Agnelli, Anthony Drexel Biddle, and George Frazier might not mean much to the average person, but Hamilton and Martorano talk about them the way basketball fans do about Michael Jordan.

Hamilton explains that one of the things he likes so much about Martorano’s clothes is the shoulder, a blend of American, English, and Italian styles, with a high armhole and a slight roping at the head of the sleeve that the tailor has worked tirelessly to perfect.

“I like to see a man’s suit have a charging shoulder.... [It] has to look like he can handle the case. If it’s kind of compressed and too small, it doesn’t look like a man can handle it.... The shoulder has to be strong but not domineering; the waist has to be suppressed but not to a point where you’re a fanatic about it.” (Many of Martorano’s customers smuggle their new purchases home to avoid the judgment of their wives, but you get the sense that Hamilton isn’t one of them.)

Gianni Agnelli, the former Italian senator and Fiat head who loved a well-cut suit, serves as inspiration for Martorano.

Martorano says that the starting point for a bespoke garment is that it should fit. He ensures things are just right over the course of four or five sessions, making Kabbalistic markings on the cloth, calling out measurements for parts of your body you’d rather forget about, and asking you, “Which way do you dress?”—the tailor’s delicate version of “How’s it hanging?”

But what customers are really paying for is a level of fresh thought that’s scarce at larger tailoring houses. Martorano has worked to find the right thickness for the pads in his suits—one-eighth of an inch, allowing for a British silhouette with Italian comfort.

Martorano isn’t shy about formality, but he’s also the first one to point out that the racks in his shop are filled with colorful, out-there items. The changing tastes of his customers—the average age is surprisingly low, at 45—his willingness to experiment, and an infusion of “young blood on all fronts” are to thank for the evolution of his business.

“It’s no longer about ‘Well, my father brought me here and my grandfather brought him.’ … It’s about ‘I read about this tailor. I read about this cloth.’ … Our youngest customers are the most educated that this industry has ever had.”

Hamilton says that if you don’t have a style, Martorano will give one to you. However, bespoke tailoring sometimes leads to a level of customization that appeals to the wacky and vulgar as much as it does to the tasteful. He has had to line jackets with Hermès scarves, and make suits out of garish brocade fabrics and fit them with custom Viagra pockets. He bemoans the tragedy of monograms and other specious hallmarks of quality bespoke clothing but understands that as long as customers are placing orders, he’s winning.

On a block that’s anchored by Carnegie Hall and otherwise maligned by the name “Billionaires’ Row,” Martorano is a man caught between art and the almighty dollar. He’s also born charmingly out of time. All of which helps explain how he sells suits that start at $7,500 ($4,500 for made-to-measure) to men who likely don’t have any legitimate reason to wear them. Most of his clients simply like the way they look.

In an age when nostalgia is at a premium and the craft is struggling, if not quite dying, people also look at buying Martorano’s clothes as a chance to own something vestigial.

“He knows the past. He knows the best dressers that ever were,” Hamilton says. Hell, for all we know, some of them probably lived in Martorano’s building.

Nathan King is a Deputy Editor at Air Mail