Murray Pearlstein

An afternoon with the owner of Louis Boston.

"This," says Murray Pearlstein, holding up a herringbone sportjacket by Isaia, a Neapolitan maker of high-end menswear, "is a case of cut and pray." That's an old Seventh Avenue expression, and it means producing a full run of a garment before you have orders for it. Gambling, in other words, on your own taste.

It is the end of an afternoon spent with Pearlstein, who sees himself as the best men's retailer in the United States, an opinion that many in the business would heartily second. And by now it is clear that the gist of his 50-year career has been about putting his chips on one number. He persuaded Isaia to buy several thousand dollars' worth of top-of-the-line cashmere and make the jackets so Louis Boston, the touchstone men's clothing store that Pearlstein has run since 1964, could get 12 of them (the only firm order) in early June rather than October. Granted, Pearlstein's money wasn't on the line (however, as he is a consultant to the Neapolitan company, his judgment was), but it was a vintage Pearlstein move. Mostly he's won—and when he hasn't, it's usually because he's been ahead of the curve. Consider.

In the early 1960s, he bought a nip-waisted, long-lapelled suit, regarded as dandyish at the time, for the store, then run by his father, who started the business in 1924. Then he created an ad that compared the suit's silhouette to that of a shapely woman. "My mother went crazy," he laughs, "but men bought it."

In the late 1960s, Pearlstein established a youthful European-style boutique in the basement of Louis Boston, which he called "Down With Louis," a not-so-unconscious slap at the taste ("expensive suits fashioned for old men") then prevailing at the store. He showcased modern French-designed suits—"boy were they uncomfortable," he says now, referring to the high armholes and body-hugging cut. They, too, were a hit.

At the end of that decade, Pearlstein became one of the first U.S. clothiers to visit Italy. "On my first trip there I got slaughtered because I didn't know what I was doing," he recalls. Still he sensed the Italians were the future and became an early buyer of Armani. "You couldn't give it away," he remembers now. "That's been my biggest fault—being too early, dropping out, then missing the party."

He was also the first American customer of Luigi Borrelli, the world's premier shirtmaker. He bought the complete line of Ralph Lauren Purple Label suits when it came out three years ago. ("Ralph is an icon, but he never did a top-quality suit for men until he did Purple Label.") What's next? Kiton, according to Pearlstein.

Pearlstein sells his customers by doing two things well. He cherrypicks the sartorial world, then puts items together to create a look, not a Look.

"We edit a line, buying in a very narrow, focused way," says Pearlstein. (He once astonished Kiton by taking 50 cashmere suits, but nothing else.) "The customer must believe we know how to help him get dressed. We pick the best, beginning at the fabric-mill level."

He also offers merchandise you can't get anywhere else. His power is such that manufacturers will customize garments for him. For instance, Luigi Borrelli makes a shirt with a high neckband collar for Louis because Murray doesn't like the way normal neckbands sink into the suit jacket.

He's relentless about keeping Louis singular, phasing out high-end manufacturers he feels are no longer exclusive enough, even when they account for a substantial chunk of business. "A store like this can't have what everybody else has," he says.

Pearlstein is 69 but looks much younger. Vigorous, big-chested, trunk-thighed, he has a prize-fighter's physique. (In fact, he did box in the National Guard and later at Harvard.) The day we meet he's wearing an Audrey Buckner tie, cutaway-collar Lorenzini shirt with a subtle herringbone twill pattern, and a double-breasted, pearl-gray, chalk-stripe Kiton suit.

"Kiton disproved everything that I had learned about clothing," he says. The revelation? The clothes don't look "perfect"—they drape to follow the line of the body. "Look," he says, showing me a photograph of a Kiton tailor at work. "They use basting stitches to create fullness and mold the chest of the suit. The tailor crosses his legs and moves the cloth over his knee to put in the roundness."

It is that resolution to remain open-minded, even in the late stage of his career, that makes Pearlstein what he is and Louis Boston what it is. And it's quite telling that after a half century, for Pearlstein modern dressing is simply a way of being yourself, albeit elegantly. "Watch," he says, waving his arms to show how the Kiton suit gives. "Other hand-tailored suits look perfect. But to me perfect is when I look natural. I'm not following the suit, the suit's following me."

For further information, contact Louis Boston, 234 Berkeley Street, Boston; 800-225-5135.