FANTASTIC VOYAGE

Designer Michelle Smith is creating a thoroughly modern Milly.

It may be 9 a.m. on a Wednesday, but mambo music is reverberating throughout the sunny Garment District loft where Milly is headquartered. Michelle Smith, the brand’s founder and designer, is walking around her office barefoot, pairing fabrics, consulting patterns, and directing her team to take a dress in a little here, a lot there. Her desk is, no offense, a disaster, overrun with piles of sketches and cards of trim, random inspirational images that she’s collected along the way. 

The spring ’13 fashion show is weeks away, and Smith is toiling in her work uniform of cutoff jean shorts and a loose black T-shirt. The collection—or the first few samples of it, anyway—are full of the brights and patterns that Milly is known for, but for the last few seasons, Smith has taken her look in a more modern direction with angular shapes, body-con dresses, and high-tech fabrics. Case in point: a prim blouse with a Peter Pan collar that would be completely innocuous, except for the fact that it’s made of perforated leather. “I’m always asking myself, `How do I take something classic and mess with it?’” Smith says.

A lot has changed since 2001 when Smith stared Milly with what was then called a “retro” take on femininity. Now sold in over 900 stores around the world, with its own boutiques on Madison Avenue in New York and Main Street in East Hampton (and nine more to open in 2013), Milly is a testament to both Smith’s singular vision and her intense work ethic. 

As a kid growing up in Connecticut and New Jersey, Smith lived what she calls “a cool, rugged, preppy lifestyle.” “High fashion was the L.L. Bean catalog,” she admits with a laugh, delving into a croissant. An accomplished artist in her teens, Smith started taking classes at the Moore College of Art and Design in Philadelphia, “It was a wake-up call,” she remembers. “I was one of the most talented artists in my high school, but at Moore, I realized I couldn’t just rest on my laurels.” 

When Smith moved to New York City to attend the Fashion Institute of Technology, she experienced a serious case of culture shock. “I was this innocent kid from the suburbs, and New York was dangerous at that time, but I loved it,” she says. “I went from being a preppy kid in moccasins to wearing club clothes—a black bodysuit with jeans, a big belt, and motorcycle boots. The city just took hold, and my tastes evolved.”

To earn money, Smith applied for a position as a salesperson at the Hermès store on Madison Avenue. (She discovered the brand by reading fashion magazines, which she had snuck into her mother’s grocery cart.) She borrowed a suit from a friend, and after hounding a manager, became the store’s youngest salesperson. “I was 18 years old and hawking Kelly and Birkin bags,” she remembers. “They had a uniform, thank God, because I could not afford a decent suit.”

After graduation, Smith applied to the Hermès offices in Paris for a management training internship; she was the first American employee to receive one. She then attended design school at ESMOD in Paris, and spent three years studying while interning at Louis Vuitton and Dior Haute Couture. “I painted watercolors for all the couture orders,” she recalled of her experience at the Dior atelier on Avenue Montaigne. “We showed them to Gianfranco Ferré, who was the designer at the time, and after he signed off, one copy would be kept by the house, and another would go to the client.”

When Smith finished school, she returned to New York and weighed two job offers: a design assistant position at Calvin Klein, and a similar gig at an outerwear manufacturer on Seventh Avenue. “Everyone was telling me to take the job at Calvin,” she remembers. “But the guy who interviewed me at the coat company is now my husband. I fell in love with him during the interview, I swear.”

A year later, the two were dating, and Smith left the company to work with the designer Helen Wang. “I saw that the things I was designing were selling well and ending up on the cover of the Neiman Marcus catalog,” she says. “I gained a lot of confidence. I felt like I had found my own voice, and I was ready to go out on my own.” Smith and her husband, Andy Oshrin, started Milly, and were married 2 years later. “The look was New York meets Paris, and the ironic vintage touch felt very new at the time,” she recalls. Barneys New York and Fred Segal immediately placed orders, and the brand was born. Twelve years later, Smith is still frequently asked, “Who’s Milly?” “It’s a nickname I created for the brand,” she says with a laugh. “I didn’t want to name my company after myself.” 

When asked what advice she would give her teenaged self, Smith gets reflective. “I really wonder, 'What kind of advice would my 18-year-old self give me now?'” she says with a laugh. “Being 18 is so great—you haven’t been burned by the world yet. When I was that age, I didn’t think for a minute that success wouldn’t happen for me. I laid down my plan, and I went for it. I wish I still had as much pluck. Now, I’m calmer, more sedate. But I guess mellowing out is part of growing up?”