She Enjoys Being a Girl! Meet the Mind Behind Milly

“No pants. No pants at all this time,” said the fashion designer Michelle Smith of Milly, standing backstage last month at her spring 2006 show at Bryant Park, as disaffected-looking models in white tank tops and jeans shimmied into her most recent creations and were suddenly transformed into—dare we say it?—ladies. Inspired by the late 1960’s and early 70’s, the collection was full of La Dolce Vita–like prints in bold canary yellows, tangerines, blues and chocolate browns. The shapes were form-flattering: tight, belted waists giving way to hip-skimming skirts.

Alongside labels like Tracy Reese, Nanette Lepore and Tocca, the four-year-old line Milly (“a nickname some people call me,” Ms. Smith said, which she likes “because it sounds sort of old-fashioned”) is becoming a favorite among stylish New York women in their 20’s and 30’s who might be venturing beyond the safety of J.Crew and Banana Republic, but aren’t yet ready to fork up for the Marc Jacobs and Prada. A Milly silk pleated skirt with yellow, brown and teal roses from the fall line retails for $260, while a black-and-white strapless cocktail dress costs $345.

“She’s tapped into what women want,” said Roopal Patel, the women’s fashion director of Bergdorf Goodman, which carries Milly, as does Neiman Marcus, Saks Fifth Avenue and a slew of high-end boutiques. “There are few designers on a contemporary level that offer really sophisticated, chic clothing at a nice price point. The woman that buys her is aware of the trends and knows what she is looking for. They’re going to her for more than just a great piece, a beautiful dress or skirt; they’re going for the staples of their wardrobe. You can buy a Milly coat and wear it two seasons later and it will still look fresh and new.

“It’s not girly-girl,” Ms. Patel added. “I think the word is feminine. The thing that’s great about Michelle and Milly is that she wants women to be chic. She wants women to look good and to be feminine. And she’s telling them that they can do it all hours of the day.”

For the past decade or so, jeans and pants have reigned supreme on the rumps of New York women, and if you were a young female designer trying to break into the biz—well, jeans and pants were the way to go (think of Daryl K., Stacey Bendet of Alice + Olivia, even Stella McCartney). But Ms. Smith, 32 and a sample-size 5-foot-4, is trying a different tack. “I’m always designing for myself and what I want to wear. It’s easier than designing for someone else,” she said over dinner in Chelsea, wearing a Milly frock from a previous collection: soft white cotton with a bright orange embroidered design curling around the midriff. It complemented her honey-colored curls. And “I think there is something appealing about throwing on a little dress,” she said “I mean, downtown girls can wear their pants and little wife-beaters, but sometimes girls like to look like girls.”

Waiting on Jackie O.

This girl, Michelle Smith, grew up in New Milford, Connecticut and Mount Holly, N.J. “From the moment she picked up a pencil, she started drawing,” said her mother (her parents and her younger brother attended the show in Bryant Park, looking a bit bewildered).

“I was always artistic, always drawing, but I really started sketching fashion in the sixth grade,” Ms. Smith said. “My mom saw what I was doing and she said, ‘Well, if you like that, maybe one day you’ll go to design school in Paris.’ The whole world sort of lit up in front of me and I thought that was exactly what I was going to do.” Though she knew nothing more about France than the words she picked up in ballet lessons, little Michelle became suddenly single-minded, stealing her brother’s Darth Vader action figure and using the fabric from the cape to make dresses for her Barbie dolls. In the summers she took art classes at the Moore College of Art and Design, studying Vogue in the supermarket checkout line and worshiping Karl Lagerfeld, along with that old warhorse Oleg Cassini.

After high school, Ms. Smith was admitted to F.I.T. on scholarship. Needing a part-time job, she borrowed a vintage Kelly-green Chanel suit from her roommate and landed a counter position at Hermès. “I used to love reading Elle magazine in high school and I remember seeing the Hermès ads,” she said. “I became obsessed.” At her previous retail gig, Ms. Smith had worked as a supervisor at T.J. Cinnamon’s in a New Jersey mall; suddenly she found herself selling exorbitantly priced handbags, even waiting once on Jackie Onassis. “She was so nice and gracious,” the designer said. “She could tell I was shaking in my shoes.”

By graduation, Ms. Smith, having picked up a bit more French, wrote a letter to the president of Hermès requesting an internship. Voila! At age 20, she moved to the Marseille district in Paris—a neighborhood she likens to Soho in the 1980’s. “Gay and artsy,” she said. “It was a magical time. The world was just sort of wide open.” After the internship ended, Ms. Smith enrolled at the Parisian design school Esmod, and became an apprentice at Louis Vuitton (this was before Marc Jacobs began designing for the house) and Christian Dior Haute Couture, where she ended up working in the grand salon overlooking the Avenue Montaigne. “That was a fairy tale,” she said. “You could look out on the street and watch the Arabian princesses coming in for their couture fittings.”

Back in New York after three years abroad, she found it hard to shake the Parisian aesthetic: “Everyone really dresses up in Paris,” Ms. Smith said. “For Sunday brunch women wear heels and skirts—it’s a different way of life. When I first moved back to New York I went jogging with a friend in Central Park. Afterward my friend wanted to stop in the grocery store, and I remember thinking she was crazy. Like, I can’t go into a grocery store in sweatpants!”

‘Good Old-Fashioned Hard Work’

Applying for a design job at Gallery, a family-owned coat company, Ms. Smith was interviewed by the tall, dark, handsome manager of production, Andy Oshrin. “I fell totally in love with him in the interview,” she said. “For the longest time, every time he walked in the room I would turn red. I worked there for a year before I managed to reel him in slowly.” They married in 2002.

While working for designer Helen Wang, Ms. Smith started noticing that the pieces she designed were selling particularly well. “I started getting confidence in my designs,” she said. “I was always afraid to go out on my own before that. And then one day I did have the confidence, and I was willing to put my money on it.”

Mr. Oshrin helped Ms. Smith execute a business plan, and she marked patterns and cut a bunch of samples herself. “We’d already been together for a number of years, and we were in love, and we knew it was going to last,” he said.

“Everyone asks how we can work all day together and see each other at home, too,” Ms. Smith said. “We have our moments, but we’re buddies and there is so much trust between us, which is important. When it comes to business, you can never know what people’s true intentions are.”

The first Milly collection was presented through a group showroom, L’Atelier, and resulted in quite a feeding frenzy. “I think our first year we had a business plan to do about $1.2 million,” Mr. Oshrin said. “We exceeded that with our first show. We ended up turning a profit in our first year.”

Milly began showing up in the movies (Gwyneth Paltrow in Shallow Hal) and in America’s living rooms via Friends, Will & Grace and Sex and the City (on the über-feminine Charlotte, bien sur). “I just think her clothes are cute and sassy and pretty and they fit women’s bodies beautifully," said Hollywood stylist Jessica Paster. “She always keeps them fresh.” The company’s sales are now on track to exceed $11 million annually, and the couple behind it recently bought an apartment in the East 70’s. “It feels very adult, it’s very exciting,” said the designer. “A few years ago I was living in a tiny studio. I think the only thing I owned was a mattress.

“One of the things I’m proudest of is that I didn’t have any connections, no fancy family background to help me,” she continued. “It was good old-fashioned hard work. Even now, I’d much rather lend a dress to some girl who is working her ass off trying to make ends meet.” She paused. “That said, I was pretty happy Jessica Simpson was photographed wearing one of my dresses last week.”

The company hopes to add accessories to a freshly launched swim line, and to open a free-standing Milly boutique within the next 18 months.

“I like to champion the women,” Ms. Smith said. “There’s a boys’ club out there—I’m not going to name names—but I like it when women are doing it for themselves.” She Enjoys Being a Girl! Meet the Mind Behind Milly