Alexandra Lebenthal, Michelle Smith, and Ellen Leikind at Socialite Poker (PMc)

On Monday evening, approximately 30 high-profile businesswomen gathered in the Maserati of Manhattan on York Street in Tribeca. But they weren’t there to buy cars. Culled from the Rolodexes of Alexandra Lebenthal and Michelle Smith, they were there to play for keeps at an event billed as "Ladies Poker Night" led by a "Poker Diva."

Though "diva" might be the wrong term. Besides Ms. Lebenthal and Ms. Smith, who are partners at the family wealth management and advisory fund Alexandra & James, the tables included Beth Bronfman, a managing partner at the ad agency View, New York Times-profiled divorce mediator Elana Katz, SalonTea’s Tracy Stern, director of Espial Capital Eva Szymanski and our instructor for the evening, Ellen Leikind.

Ms. Leikind, who turned to cards after years in the Fortune 500, is the author of a book called PokerWoman. "My mother taught me how to play when I was a girl, but once I entered adulthood, I was never invited to the table,” she told the Transom. “It was such a boy’s sport, much like corporate America. And I decided I wanted in."

The petite Ms. Leikind was wearing a cast on her leg, obtained after slipping on the ground outside of a casino. “But I had won $13,000 that night at the tables, so I was just happy to keep the money.”

Ms. Smith shared a similar sentiment. "The boardroom is always a men’s club, and the ultimate man sport was golf. Poker was the man’s game. But poker is so much about the skills you’ll need to compete with men. It’s about learning how to take risks, how to assert yourself, and how to see those nonverbal signs that people give off and adjust yourself accordingly." Then she slipped in the news that she had won $30,000 on a recent trip to the Bellagio in Las Vegas.

We picked up the pamphlets in front of us on the table, which—in addition to explaining what a flush is and what "calling" refers to—contained a Cosmo-esque personality quiz. Were we the type of person who thought the highest compliment was that we “took charge” or that we “worked well with others?” Did we like to decide where to take friends for dinner, or did we go with the flow? It wasn’t too hard to figure out the point: in the world of poker, being sugar and spice and everything nice wouldn’t get you anything except an empty wallet.

When it came time to play, the Transom thought it would be a breeze. In less than 10 minutes, we were the only person in the room without any chips. In an effort to show how aggressive we were, we had refused to fold ... ever. It also didn’t help that during the first round we got confused and thought we were playing blackjack.

But we did everything we were supposed to. We gambled assertively and took risks. Why weren’t we the CEO of an investment firm yet?

"Well, you see that kind of behavior more often in men,” Ms. Leikind sighed. “Sometimes people will just do what they want, no matter what you tell them at the table."

Alexandra Lebenthal

Wealth managers Alexandra Lebenthal and Michelle Smith know when to hold ’em and know when to fold ’em, and they host a quarterly women’s poker club to show off exactly how good they are at high-stakes betting. Among their fellow poker players, who find Maserati of Manhattan a more relaxing and pleasant staging ground than Vegas, are Guest of a Guest founder Rachelle Hruska and Gotham editor in chief Samantha Yanks ... Meanwhile, Mikhail Baryshnikov hosts a private cocktail reception for “The Art I’ve Lived With,” a gallery show of his broad collection of largely Russian art. Lucky guests will get to compare Jean Cocteau’s portraits of Diaghilev and Nijinsky with the living, breathing Mr. Baryshnikov.

Ladies Poker Night, Maserati of Manhattan, 1 York Street, by invitation only; “The Art I’ve Lived With” opening, ABA Gallery, 7 East 17th Street, #2, tonight’s opening by invitation only, show runs from December 4 to 15, Tuesday to Saturday, 12pm to 5pm.

 In the past, Ms. Smith has been influenced by other locales.

"Sometimes I veer off and have French inspirations from my time spent in Paris and that sort of thing, but I live on 75th on the Upper East Side, and I love my life there. And I was thinking, ‘You know what? I’m just going to stick close to home and let my backyard be my inspiration.’ I really feel like getting dressed up this season.’"

The designer suggested hopefully, as fashion types will, that uncertain markets, rather than squelching the demand for adornment or sending us in a more subtle sartorial direction, have only enhanced our appetite for luxury.

"Because the economy’s only so-so, I think it’s really important to offer beautiful pieces," she said. "If you’re going to spend money on clothes, I think it’d better be very special. So I’m doing very pretty, very opulent clothing in very luxurious fabrics."

And no heroin-chic models, please: "I like the fresh, pretty face," Ms. Smith declared. "With the uptown inspiration I don’t want it to be fuddy-duddy or too classic. And most importantly, girls who can walk. You’d be surprised how many models can’t walk."

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.”