Michael Druskin, president of Twin Cities fashion retailer Len Druskin, Inc., insists he has no interest in naming a store after himself. But since he took over his father’s eponymous Edina boutique 14 years ago, he has opened 10 more—all named after his dad. Now he is poised to take Len beyond state lines.

Keeping up with the Druskins in recent years requires a glossary. There’s the flagship Len Druskin store at Galleria, which features designer fashion, footwear, and accessories for women and men. At Gaviidae Common in downtown Minneapolis, the brand is split among three storefronts: Len Druskin Man; LD Len Druskin, for women’s professional and dress apparel; and LD Blues, for women’s upscale casual. The “Len” stores are the fastest-growing division, with five stores at Twin Cities malls, delivering contemporary fashion at a lower price point (store motto: “Always 50 percent off”). But they’re different from the Len Druskin Outlet at City Center, which serves as clearance centers for the higher-priced, designer-driven Len Druskin stores at Galleria and Gaviidae.

In all, the family-owned company—with no outside investors—operates 11 stores from Ridgedale Center on the west side of the metro to Rosedale Center on the east. That’s three more than Hot Mama, another Edina-based boutique-turned-fashion chain, which now has locations nationwide.

Michael Druskin is not afraid to take a chance, like a pop-up store at Maplewood Mall that closed earlier this year. He’s a staunch supporter of downtown Minneapolis, opening stores when everyone else seemed to be fleeing. With a total of five downtown storefronts—besides the three at Gaviidae, there are two at City Center—he now waits to see what direction new owners will take both buildings.

“Downtown is more challenging than other locations, but we’d like to remain downtown,” the 43-year-old Druskin says. “We plan to continue operating our current stores as long as there is retail in those buildings and we continue to have customer support.” But he isn’t idly waiting for Minneapolis to solve its shopping hang-ups. He has his sights set on taking Len to another market this year. “It’s been a goal of mine for a few years,” he says. “We feel the time is right to test another market.”

It’s difficult not to conclude that Druskin is eyeing Chicago, of course—the only Midwest market with better retail demographics than the Twin Cities—but he’ll only say: “It’s a market we are most familiar with. We’d like to go somewhere where we could have a cluster of stores somewhat like our setup in the Twin Cities.”

The big question is how it will play in a city that doesn’t know Len Druskin: the brand, the man, the career retailer. Then again, the average Len customer at Mall of America probably doesn’t know there really is a Len, either, and that doesn’t seem to hinder sales of skinny jeans and mini dresses.

It Started With Len

Len Druskin’s retail career dates back to his high school days in the late 1950s, when he sold shoes at Bakers. After graduation, he became a buyer for Dayton’s and then Donaldson’s. In 1976, he opened his own boutique at 50th & France with the help of his mother-in-law, Sally Shiner, who had been a popular buyer for Jackson Graves. In the early 1990s, Druskin moved to the Galleria, where, at 73, he is still a daily fixture on the sales floor.

Len Druskin calls himself the company concierge, chatting with customers, handing out bottled water to the parched, animal crackers to children. He’s quick to connect the dots from young shoppers to their mothers and grandmothers, to whom he once sold mother-of-the-bride and bar mitzvah dresses. Druskin is nostalgic for the days when specialty stores were defined by their omnipresent owners. “Today, owners aren’t as connected to customers,” he laments.

The way his son sees it, these days you need a national infrastructure to make a local impact. Michael opened a New York buying office for Len Druskin a few years ago and recently hired two Los Angeles-based buyers. That bicoastal presence allows the company to respond quickly to trends and customer feedback.

The collection of stores generates between $10 million and $20 million in sales, according to Michael Druskin, who says sales have doubled in the past five years, fueled by new store openings. “We hope to grow at 20 percent a year for the next few years, with new revenue coming from both new stores as well as better productivity out of our existing stores,” he says. To that end, several Twin Cities locations will be remodeled this year, and branding will be refreshed.

The Druskins remain steadfast about funding growth through cash flow. “Like so many other small retailers, we struggle with the cost of rent and other day-to-day expenses that keep rising,” Michael Druskin says. “We just have to try and buy smart and keep our merchandise turning. Sure, it would be easier if we had backing, but doing it this way forces us to make choices, and sometimes that is not a bad thing.”

Overall, Len Druskin, Inc., employs 100—including Len’s wife, Susan, who does some bookkeeping, and grandson Brody Ryan, who recently started working part time at the new Ridgedale store.

A Taste for Fashion and Risk

Despite his father’s name on the doors, Michael Druskin is in charge, overseeing everything from store management to buying to expansion plans. “I love the challenge of it all,” says Druskin, who cut his teeth on buying trips with his father when he was a kid.

“The most important thing in a family business is to have boundaries and respect,” Len Druskin says. “Whatever Michael chooses to do, I support it.”

That included some eyebrow-raising decisions when Michael first took the helm in 1999 after a short stint in the corporate offices of Toys “R” Us as a financial analyst. He abruptly shifted focus at the flagship Galleria store, from special occasion to casual, contemporary apparel. Upscale shoppers were starting to dress down, and he sensed the category was underserved in the Twin Cities.

Ultimately, he was right, but replacing ball gowns with jeans and T-shirts overnight was a mistake, he now admits—and one that might have killed the company in today’s post-recession climate.

“I always tell him, it’s OK to make a mistake,” Len Druskin says. “If you realize something isn’t going to work, acknowledge it, correct it.”

Sometimes, it just takes conviction. Len recalls opening the first box of Juicy Couture velour tracksuits his son had ordered when celebrities were beginning to wear them. “I remember thinking, ‘They’re too small. They’re not going to fit anyone.’ ”

They sold out in days.

Same thing happened in 2001 when Michael introduced the Twin Cities to Seven jeans, one of the first brands to normalize $100-plus denim. “We sold eight pair in the first 45 minutes,” he recalls. “It was a defining moment.”

His vision, while more exacting today, was clear from the start of his tenure: fashionable clothing that is wearable. “We never go overly trend,” he says. “Our customer wants to be comfortable.”

It’s a philosophy that plays to both 20-year-olds and 50-year-olds, observes Mary Van Note, a retail analyst and partner in Minneapolis-based Ginger Consulting and a Len Druskin patron.

“I think Michael has a great eye for stylish, casual clothing that is not too hard to wear and hits a good price point,” Van Note says. “It’s rare to find a local boutique chain with such fashion authority.”

But good instincts aren’t enough in the age of social media and online shopping. Fashion emporiums such as Netaporter.com and Gilt.com make it possible for anyone, anywhere, to access the latest trends as they hit the runway.

“No one can be first anymore,” Michael Druskin says. “Now, it’s about speed from vendor to floor and the way you put it together. We can pick and choose from individual brands. It’s more about the assortment than exclusivity.”

And service, his father chimes in. “We work for the customer,” Michael echoes. While Len takes time to engage with each customer, Michael seems always to be moving in five directions at once. But he’s also listening, observing, and taking chances—like the discount division, which started by accident.

Two Brands, Same Customers

It was 2004 and the stock room of the Galleria store was overflowing. He temporarily took over a vacant space in Galleria for a clearance sale. It became a seasonal event, which moved across the street to Southdale. The response was so strong, Druskin started purchasing overstock and taking it directly to the outlet so he could keep the store going year-round.

The outlet business opened the door in 2006 to the lower-priced Len division, which positioned the company to prosper during the recession and beyond. Value has become a critical part of the fashion equation, Michael Druskin says. “As long as the customer supports high-end fashion, we will sell it. But they’re thinking about the quality of the fabric and the number of times they can wear it. People mix and match today.” That’s why the company finds many customers shop both Len Druskin and Len stores. “It’s not that different than Nordstrom and Nordstrom Rack”—just a few more initials and nuances, perhaps.

“We’re trying to simplify,” says Michael Druskin, who has taken his fair share of ribbing for the many iterations of his brand and the density of product on their shelves. The Len Druskin Outlet serves its purpose for unloading last season’s merchandise while maintaining the no-sale mystique at the flagship store. But the future is in the Len division. That mix of boutique atmosphere and service, along with bargains on first-run trend apparel, has made Michael feel like the Len brand could have legs beyond the Twin Cities.

“I don’t think we know yet how much growth we can sustain,” he says. “It’s constantly changing. There’s always another idea.”

Allison Kaplan covers Twin Cities retail for MplsStPaul magazine.