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Going With the Gut

Debi Greenberg is anything but shy. Savvy and opinionated, the owner of renowned luxury retailer Louis Boston is not afraid to take chances.

BOSTON — Debi Greenberg is anything but shy. Savvy and opinionated, the 51-year-old owner of renowned luxury retailer Louis Boston is not afraid to take chances. “I just have the guts to go ahead and do things,” she says over a lunch of salmon and sake at Louis’ new restaurant, Boston Public

“I changed the silhouette of our suits back in the mid ’90s—I just decided we weren’t going to have any more pleats in the store because they were over,” she says. Greenberg also boldly dropped Zegna suits from the merchandise mix in 1996 after deciding that work-force suits were less relevant. “My consumer has never regretted that decision and I have never regretted that decision.”

This ability to fearlessly follow her instinct has allowed Greenberg to keep Louis’ merchandise ahead of the curve and land it on ‘the where to buy’ pages of almost every fashion glossy from Vogue to GQ. It’s an invaluable skill she learned from her father, the legendary retailer Murray Pearlstein, from whom Greenberg took over Louis in 1997.

“He taught me a lot about gut, about the confidence of just feeling it and going with it,” she says. To this day, Greenberg only writes orders at an appointment. “You ask the questions, you do the merchandising and work out the puzzle there and then, because that is when you have the most gut.”

Housed in the former Museum of Natural History building in Boston’s historic Back Bay neighborhood, Louis’ stately brick facade disguises the clean, modern aesthetic of the store’s three-floor, 40,000-plus-square-foot interior, which also features women’s and home departments, as well as a music bar and optical shop. Clean, light-wood floors, statuesque white columns, and towering arched windows serve as the perfect backdrop to showcase Louis’ eclectic assortment and creative displays.

Started by Greenberg’s great-grandfather, Louis Pearlstein, in the late 1800s, the original store was not the high-end retailer it is today, but rather a small pawnshop that specialized in the mending and resale of immigrant clothing in nearby Roxbury, Mass. In 1929, inspired by their father’s love of clothing, Louis’s two sons, Saul and Nathan, opened a small, upscale, made-to-measure shop in Boston and named it Louis. Murray Pearlstein took the business over upon graduating Harvard in the ’50s, using his impeccable sense of style to turn Louis into the luxurious, well-edited retail institution it is today. “He was one of the first people to go over to Italy in the late ’40s and discover off-the-rack clothing, which is what most people are buying today,” Greenberg says, sipping a cappuccino. Much like Louis’ sales associates today, Pearlstein was known to push his customers to take chances on new looks and labels. But nowhere is the family legacy more apparent than in the sophisticated yet masculine selection of Louis’ merchandise.

“My father always looked great, he wore beautiful clothes, but the look was never perfect, never studied. He would always have on an amazing shirt and tie, but you couldn’t really understand how it went together,” says Greenberg. “He also taught me passion for fabric, and cut—a jacket can be tailored beautifully, but if it doesn’t have that sexiness, that special thing, it’s not going to work.”

Striving to achieve that mix of effortless chic and exclusivity, Greenberg searches for clothes with proportions, great fabrics, and enough individual details that her customer knows it possesses “that special thing.” She does not attend men’s fashion shows, and rarely picks up lines at trade shows. “I watch people, I take the subway, I get out on the street and I look at the way people are dressed.” And when a label does spark Greenberg’s interest, she buys it by category. “I’ll look at a Neil Barrett sport pant, and take a Dries van Noten sport coat and a phenomenal Kiton jacket.”

She approaches Louis’ merchandising in a similar fashion, mixing designers and categories, creating a feeling of entering several well-edited closets with little focus on labels. “Men simply do not care about designer brands—the minute you speak to them in those terms, they tune you out,” says Greenberg, ascending the elegant central staircase to the second floor, where jackets by Kiton hang next to pants by Valenti and shirts by Fray and Brioni. Beautiful leather belts and shoes by Henry Beguelin, and leather bags by Zagliani sit atop white wooden dressers nearby. Glass tables display shirt, tie and sweater pairings, and an impressive flat-screen television and clubby leather chairs lead men to a back wall of shoes by Harry’s of London and Tretorn. A separate sport coat room and suit room are set off the main floor, and an open-air mezzanine level houses a denim room one floor above. Casual weekend wardrobe options, including shirts from Steven Alan and Oliver Spencer, T’s from Rag & Bone, and pants from Transit, hang along the perimeter of the outer balcony.

The secret to Louis’ success is its unique approach to men and retail. “You have to have an opinion as a store, and we offer men a point of view—guys don’t want too many choices—they are so afraid of so many things and we offer them direction,” explains Greenberg.

In addition to Louis’ signature merchandising, the store’s sales associates, who do not work on commission, double as personal shoppers, guiding men of all ages through the shopping experience. Trained to build relationships with customers —80 percent of Louis’ business is done with 20 percent of Greenberg’s customers—Louis’ sales associates put together an entire package for a client, not just a single suit or tie. Associates talk to customers about their lifestyles and needs, and they’ll even go so far as to put a video together and give styling advice via e-mail. And they do it in a timely manner.

Yet Greenberg is the first to admit that her core customer, much like her store, is far from ordinary. Wealthy, sophisticated Bostonians of all ages, some who’ve attended graduate school in the area, or made it big in bio-tech or finance, make up much of Louis’s business, which generates anywhere from $18 million to $20 million a year. “I don’t have to be everything to everybody,” she explains. “My customer is an entrepreneur, not an emulator, and he is pretty successful.” The majority of the clothing she carries is handmade, and her most expensive suits sell out before the more reasonable versions.

Although Greenberg acknowledges she is still trying to find ways to captivate the male audience, she also knows she is on to a successful retail formula. “Louis has a great sense of discovery,” she says. “Retail has become so formulaic and if you are going to go to a place like Louis, it has to entice you. We want to make sure we push men forward a bit and educate them.” Greenberg was the first specialty store to hire a DJ and incorporate a music bar in 1999, because she knew it sparked men’s interest.

A trailblazer like her father, Greenberg is not resting on her laurels. Her latest venture? Relocating Louis—with a possible spa and bakery included—to a new location in Boston by 2010. Greenberg said Newbury Street, once the only address for upscale boutiques in Boston, has become predictable. “It doesn’t suit my customers anymore. All the shops here used to be unusual—now I have an H&M and a Filene’s Basement down the street from me.” She is looking at raw spaces to convert in Boston’s trendy South End neighborhood, as well as waterfront properties that have opened up since the recent completion of the Big Dig project.

“You know what, it may not work,” says Greenberg, “but I’m a third-born child and I am not afraid to fail.”