Turning Point

Debi Greenberg really does not want to be here. She’d rather be anywhere else, doing anything else, than talking about herself. For weeks, she feinted around this interview, and even now-her PR rep securely by her side-she flinches at the sight of the black tape recorder on the white table linen, the red glow of the record button a most uninvited guest.

It’s an odd reaction from a woman undeniably at the top of her profession, a woman who not only owns Louis Boston-the ninth-largest independent specialty store in the country-but also has single-handedly revitalized the aging, third-generation haberdashery.

“I don’t, I didn’t, want to do this,” she says as she nimbly works a mound of tuna tartare with a pair of chopsticks. “I don’t want to see my soul. I like the way I see myself from the inside out. I want to be comfortable in my skin without having to analyze it from the outside.”

But there’s no getting around the general public’s critical analysis. Since Greenberg purchased Louis Boston from her father last year, the changes she has made in the clothing and accessories store have been both radical and very visible. And let’s be honest: Bostonians don’t like their institutions messed with. Not only has she replaced the store’s adjoining and widely loved Café Louis with the Asian-inspired Restaurant L, but Greenberg has also overhauled the first floor with wares that are raising more than a few eyebrows. Instead of the men’s sportswear of years past, there’s now a packaged food corner, a luxury bed and bath section, and-most controversial of all-a DJ spinning tunes in the very store where Boston’s Brahmins bought their Italian-cut suits for years.

In a world of Wal-Mart homogenization and retail mallification, Greenberg’s vision-to sell high-priced, one-of-a-kind specialty items, many by designers most consumers haven’t even heard of-is unorthodox, to say the least. She rejects the fashion show circuit and, in her resolve to remain unique, dumps any label that begins to sell to big department stores. Greenberg says it’s “communism” to give her customers what they say they want. She insists on selling them what she likes.

What remains to be seen is whether flouting today’s retail reality will make or break the legendary store. Its sales floors, with their racks of $2,500 suits (even T-shirts cost $100), seem rather quiet these days, leaving folks to wonder: What is the future of Louis Boston, anyway, and who is this woman running it?

The answer is not what you’d expect. Looking more laid-back Santa Monica Boulevard than seamlessly tailored Newbury Street, Greenberg wears little jewelry and even less makeup; her hair is a long, natural sandy-blond tousle that she plays with like a teenage girl. Rather than the industry uniform of severely tailored black, her neutral Marni blouse is flowy and her calf-high Prada boots are low-heeled. Over our three-hour talk, she never once slips into the obscure, self-important language of style’s “editrixes,” opting instead to slice through the frilly world of fashion with a sharp intelligence. Truth is, it’s hard not to like her. She’s like the coolest girl in high school, the friend you hammered back shots of tequila with.

And yet, there’s no denying it: Debi Greenberg is a polarizing figure. While one coworker says she could never work for anybody else, a former employee says she is a “total bitch.” Even her biggest boosters, who call her a visionary, concede that she’s tough. Really tough. “She told me, ‘I don’t care what anyone says to me,'” says Gretchen Monahan, owner of the upscale clothing boutique Gretta Luxe. “You get that toughness right off the bat. If nothing else, Debi Greenberg is going to give it to you real. But she really turned the store on its head, and it took a lot of guts.”

Louis Boston has always been a study in gutsy evolution, and a reflection of its owners, ever since Greenberg’s immigrant great-grandfather, Louis Pearlstein, opened a pawn shop about a century ago in Roxbury. He’d put cash in men’s pockets in exchange for the suits off their backs, then re-sew those suits and resell them. His sons, Nathan and Saul, took over the store in 1929, named it Louis, and started selling custom-made clothing from New York. By 1950, Saul’s son, Murray Pearlstein, took over and converted the custom-clothing shop into a retail store.

Even then, Murray Pearlstein realized that Louis had to evolve if it was to survive in the cutthroat world of retail. “I had tremendous conflict with my parents,” Pearlstein told this magazine in 1998. (He declined to comment for this article.) “[My father and uncle] were two guys who were very afraid. They just wanted to hold on to whatever it was that they had.” Not Murray. In the ’60s, he was one of the first to import high-end men’s labels from Italy. Even then, he battled the initial resistance of his customers. “I had tremendous conflict with our clientele because I was bringing them things that cost four times what they were used to spending,” he said. “And yet it worked.”

Murray’s children-Greenberg and her brother and sister-grew up in a world different from that of their teenage counterparts in conservative Chestnut Hill. They often traveled to Europe with their father, who was more dapper, European, and youthful (he actually jogged back then) than most dads. Her mother was, as she puts it, “ahead of the curve” fashionwise, wearing Halston Ultrasuede before anyone had even heard of it. This rubbed off on Greenberg, who claims to have never followed mainstream trends.

After graduating from high school, Greenberg spent a year skiing at the University of Colorado (“No one told me that you had to study, too,” she says, laughing) before heading home to Simmons College and earning a marketing degree in 1978. Though her sister, Nancy, jumped right into the family business in the early ’70s-launching the women’s department-Greenberg spent the next 15 years working at Boston advertising agencies, going to discos, and meeting and marrying her husband, Mark, who runs the New England Tractor Trailer Training Schools.

But conflicts between the third and fourth generations of the Pearlstein family ignited just like those between the second and third. Nancy had a falling out with their father-they were too much alike, is all Greenberg will say about it-and left in the early ’90s to open her own boutique in Maryland. Greenberg came in as a buyer at Louis, and the two apparently haven’t spoken since. (Greenberg has never set foot in her sister’s store, and Nancy has never met Greenberg’s 12-year-old daughter, though the reasons for their rift aren’t clear. Their brother, Steven, a business columnist at the Washington Post, says only: “Family businesses have a way of getting in the way of relationships. This is not a good subject for me to talk about.”)

Though Murray has been described as a difficult man to work for, he did, unlike his own father, give Greenberg the autonomy to make changes. Louis had been dominated by marquee Italian designers (it was one of the first stores in America to offer Gucci, Prada, and Dolce & Gabbana), but Greenberg, realizing that the retail market was crashing and the store needed to shift gears to lure a younger clientele, dropped some of the biggest-name designers and mixed the men’s section by category instead of by collection. She also started moving into independent and small-batch high-concept labels for women. These were profound, yet quiet, changes. The store was becoming more independent, just like the woman who was shaping it.

Greenberg doesn’t do fashion shows. “Oh my God, the drama of who’s sitting where,” she says, laughing. “Shuffling everybody in the front row, and it’s like, ‘They are killing kids in Iraq.’ Who cares about any of this? It’s just so irrelevant.” To be sure, she doesn’t do a lot of things convention says she should.

Debi Greenberg is not a conventional person and she knows it, admits it. “I look at things completely differently than anybody else, and I’m not afraid to tell people that I think it’s completely odd the way they look at it,” she says. She lists this, freely, as one of her faults-a list that also includes her aversion to forgiving people. “I never got that concept down,” she says. It’s a quality that gets her into trouble. “She has a lot of enemies in the fashion industry. They find her obnoxious,” says one industry insider who admires Greenberg. “She’s tough. She hasn’t always endeared herself to people, because she says it like she sees it.”

Not everyone sees that as a fault. “The thing I like about her is that you really know where you stand,” says Los Angeles designer Gregory Parkinson. “She instantly knows what she’s doing. There’s a firmness, she can be intimidating, and she doesn’t mince words.” Adds New York-based designer Alice Roi: “She’s very outspoken, very clear and very direct-which is really refreshing in the fashion world, where people can be so fake. She has no problem telling me what she doesn’t like. Her direct approach is so much better, it’s cutting through the bullshit.”

Ask anyone about Greenberg-supporters and detractors alike-and they’ll say the same thing: She has a very clear and concise vision. In an era of cookie-cutter department stores pig-piling on trends, she wants to sell only those things that are unique and special. “I’m looking for something that’s going to surprise me,” Greenberg says of the clothes she buys for her store. “I’m looking for a certain naiveté more than anything. There’s a certain innocence to the way something’s designed that I’m really looking for.”

That’s why she rejects the glitzy shows in favor of slapping on her headphones and scouring the young, hip neighborhoods of Milan and Paris and London. “To find out what everybody wants takes all the soul and gut out of everything, and hence you have Wal-Mart,” she says. “If you give the consumer what they say they want, it’s communism.” Greenberg wants to give her customers something they don’t even know they want. She does that by looking for what appeals to her. “You have to be pretty brave to say, ‘This is it,'” says Alicia Gordon, whose agency, Gordon Lower, used to do PR for Louis. “She delivers an individuality that’s vanishing. It’s not for everyone, but I don’t think Debi is worried about that. Quality and workmanship and design-they are not in large supply right now, and she wants to keep that alive.” Adds Gretchen Monahan: “She’s really clear about her position, that she’s not going to give way to generic, mainstream fashion. It’s about her likes and dislikes.” (Her father was the same way. One customer remembers walking into the store one day and finding all the salesmen in collarless shirts without ties under jackets with no pockets. Pearlstein declared, “That’s how everyone will dress from now on,” remembers the customer, who, unfortunately, had come in to buy a necktie.)

This is what puts Louis on the cutting edge, though sometimes to its detriment. “She’s so ahead of the curve, to the point that some people don’t understand it,” says Louis vice president Maria Fei. “Like Marni. When she first bought it, it wasn’t accepted, but then she watched it flourish. Now Jennifer Aniston talks about it, and it’s on Sex and the City. She’ll take a risk on young designers that other companies who have to watch their bottom line wouldn’t.”

It’s why young designers love her. “For any designer who is not American and wants to enter the U.S. market, Debi is the first stop,” says Parkinson. “She’s not afraid of difficult product because she believes consumers need to be educated, to be told what to buy.”

Staying ahead of the curve brings other problems. For one thing, it’s hard to remain exclusive in a global market. “Exclusivity is important,” says Greenberg. “I have fights with my vendors about it.” It means dropping labels when they become available in department stores and dumping designers who sell out to big houses. It means finding clothes not available anywhere else. It can also mean losing customers. Louis “has a reputation as one of the few remaining large, independent stores supporting avant-garde fashion,” says Los Angeles Times fashion writer Booth Moore. “But, no offense, I really can’t imagine who is buying the stuff in Boston, and I was a bit dismayed to see the racks so full so far along in the season.”

“In spite of Boston we manage to do okay,” says Greenberg. Nor are her customers exclusively Bostonians: Bruce Springsteen, for example, shops at Louis when he’s in town. At any rate, few people really think it’s about the money for Greenberg-or even about upholding tradition and history. “For her it’s really, really personal,” says Monahan. “It’s making her mark and saying ha to the naysayers.

This is our R&R room,” Greenberg says of the first-floor of her store, which brims with luxurious bed and bath imports. She picks up a $35 towel from the White House of London, and shows how it’s neither too piley nor too heavy. “I analyze everything,” she says. “If I’m going to carry it, it’s got to be perfect.”

As she sweeps through the newly overhauled main level of the store, now a marketplace for lifestyle products, it’s clear the place is a direct reflection of Greenberg’s taste. There’s the “Music Bar,” a showcase of CDs picked by DJ Felix Cutillo. “It’s a wonderfully welcoming feel for people who are normally intimidated by the store,” she says. There’s a Bonnie Benrubi gallery, its stark white walls housing framed black-and-white photos. “I collect vintage photography,” Greenberg says. “Is it productive? Probably not, but it gives an element that I wanted.” There are all kinds of fancy foodstuffs, from Dean & Deluca candy to Fauchon chocolates, plus vintage linens, pots and pans from Paris, even a Morgenthal Frederics eyeglasses boutique. “We did have antiques. But it didn’t work. I wasn’t afraid to fail,” she says matter-of-factly.

Greenberg is going by trial and error, and sticking to her vision. “I really want to keep this store a discovery,” she says. And, just like her father did when he made sweeping changes in the ’60s, she is encountering resistance. She admits she’s lost some of her older clientele but says she’s seeing more young people walk through the doors. “The people who shop here have to be entrepreneurial,” she says. “They really want to express themselves in a way that not everybody else is doing. I’m always looking to evolve and innovate. I like traditions, too, but some people wallow in it.”

But Boston is all about its traditions, and perhaps that’s why Greenberg is judged so harshly. “She has a vision that’s beyond Boston. She should be in Manhattan or Paris,” says the fashion industry insider. “She’s a rarity.”

It’s a few days before Louis Boston’s end-of-the-season sale, one of only two times of the year the store marks down its prices. Walking through the racks of women’s clothing, Greenberg picks up different pieces and bemoans that they haven’t sold. She calls the sales racks her “palette of failures,” yet it’s clear she doesn’t really believe that. “Why didn’t you buy this?” she says out loud to an imaginary customer. “I don’t understand why.”

For Debi Greenberg, apparently, failing isn’t such a big deal. There were the hard-to-find sneakers, the Nike watches from Japan, the Balenciaga bomber jackets-failures one and all. “If it fails, I’m okay with that. I’m a third child; I don’t care if I fail,” she says. “Failing to me is not a big issue. Not trying is a really big issue.”

And that about sums it up. It’s why she’s steadfast in sticking to her vision, no matter what the outcome. It’s why, as she puts it, it’s a great time to be in retail, even though it’s a terrible time to be in retail. “Because you can fail anyway, so you might as well throw it out there,” she says. “You might as well pioneer some new way of doing it because there’s nothing more fun than pioneering a new idea and having it work.”

Who knows if it will work? But tomorrow she’s headed to Europe to buy a new collection for the store, because in retail, you’re only as good as the last season. “You’ve got to want to go out and start all over again,” she says. “That’s the part that I really love.”

She’s going to Europe alone. She used to have other people accompany her, but they all eventually left. “I know it’s short-sighted of me,” she says about not training replacements. “But I guess I’ve been hurt.”

It’s the only time she shows vulnerability, and Greenberg knows it-it’s why she didn’t want to be here today. Then she becomes defensive again. “I already know all my faults, I really don’t need someone to tell me about them,” she says. “If you want to know them, I can sit here and I can list them for you. I’d rather they come from me than from someone else. . . . I just don’t want a million people reading about them.”