filthavenue:

Scott Sternberg, a former Hollywood talent agent, is pushing to turn his small, successful label into a fashion empire.

Formerly with Creative Artists Agency, Mr. Sternberg quit his job seven years ago to launch the label Band of Outsiders, spawning a boom in skinny ties and riding the surge in modern prep wear. “It’s on the floor adjacent to Gucci, Lanvin, Bottega Veneta and Thom Browne, which is an impressive accomplishment for something that’s a small niche brand,” says Tom Kalenderian, executive vice president of menswear at Barneys New York. Last year, Mr. Sternberg, who has little design training, won the best-menswear-designer award from the Council of Fashion Designers of America in a tie with Calvin Klein’s creative director.

Mr. Sternberg accepted the award, but the 35-year-old cultivates an outsider image. Actor Jason Schwartzman—not exactly a Hollywood hunk—is the face of the brand, and Mr. Sternberg abets his scrawny, slightly nerdy appearance with bulky prescription glasses. He remains adamant about living in Los Angeles, even if it means missing some of the New York fashion social scene. “If I was here in New York in this mix influenced by the same thing all these people are influenced by, the edge would be gone,” he said in his Manhattan showroom. “This [L.A.] bubble is vital to being able to do something that is not informed by fashion.”

That doesn’t mean Mr. Sternberg lacks in ambition. Despite the downturn, he is plotting to transform the $12 million business into a $40 million one over the next three years. To do that he’s taking on the highly competitive world of women’s wear; he is in the midst of expanding Boy., a menswear-inspired women’s collection launched in 2007 with prices that range from $135 for a T-shirt to $1,750 for a “boyfriend” blazer. His second women’s line, girl., a less-expensive line with more feminine touches, is in the works.

Because women’s fashion trends change at a faster rate, Mr. Sternberg, who has most of the brand’s tailored clothing handmade in Brooklyn, struck a deal last year with Italian manufacturer Pier SpA to produce Boy., and is upping the number of women’s collections to four per year from two. He has also been busy for the past few months meeting with equity investors to secure a round of financing to help with the expansion. Though investors have been generally skittish of investing in designer brands, Mr. Sternberg said these discussions have been going well.

Band of Outsiders’ success has been somewhat surprising, as the clothing is hardly unusual fashion-wise. Mr. Sternberg, aware of criticism that his clothing is nothing more than an upscale version of J. Crew, upped the drama quotient for his women’s line. For his fall presentation of Boy. during New York Fashion Week, Mr. Sternberg threw in pieces like a bandage skirt made out of neckties, a grey wool cutaway blazer with a fox fur shawl collar and quilted skirts. Reaction was generally favorable. Fashion boutique Opening Ceremony blogged that “there was much to be adored at Scott Sternberg’s Boy./Band of Outsiders presentation.”

Observers wonder whether a label which prides itself on being outside the mainstream—and doesn’t advertise in major media—can grow without damaging its indie-cool factor. “The challenge is sustaining the buzz while recognizing merchandising and price-point realities and growing distribution without undermining the perceived exclusivity,” says Joshua Sparks, a business-strategy consultant to fashion brands and former chief executive of Thom Browne. “It’s a pretty delicate dynamic.”

Mr. Sternberg said the clothes and the label’s vibe are not “tactics” to create buzz, but rather his personal expression. “I’m just trying to maintain an honest and growing dialogue with people. Over time, the plan is to offer a wider range of products and price points, and I don’t think that at all compromises the dialogue.”

Meanwhile he has launched more commerce-minded initiatives that still try to maintain the brand’s trademark idiosyncrasy. In January, he launched a line of fitted polo shirts entitled “This is not a polo shirt” with prices ranging from $130 to $175, less than his main collection, where button-down shirts start at $220 and handmade suits cost about $2,000. The label has also opened an online store, but instead of a standard virtual shopping cart, there’s a menu that reads “Drag stuff you might buy in here.”

“We knew it was different from what was out there, but it was the right approach for us,” Mr. Sternberg said.

(Editor’s note: Couple points I wanted to add about the label…I own three blazers and they are amazing (thanks to the tailoring of Martin Greenfield in NY), they need to make longer shirts you can tuck in as I’m too tall and I hate exposing my fleshy undersides every time I raise my arms, oh and YMFY is on the Not a Polo Blog!)