Confidence can take years, even decades to get just right. “As a teenager I was totally insecure because my sister always looked better than me,” says FOF Jane Meryl. “I used to wait until she left for work and raid her closet.” Today, Jane has come into her own style, one that she feels good about. “I call it ‘sophistiphunk;’ hip but comfortable, a free spirit yet very down to earth. And it’s important I always look approachable.”

“It was my Sweet Sixteen, April of 1967 at a restaurant on Fordham Road in the Bronx called Hillmann’s. I remember my mom getting up on a table and singing “Let Me Entertain You,” lifting up her dress and showing her red girdle. My friends made me a stupid hat from the gift wrappings that they said I had to wear. Most of my gifts were sweaters and my mom was constantly telling me to smile.” —FOF Jane Meryl

FOF Lib McPherson believes that “personality as well as specific events in life,” should dictate a woman’s style, not fleeting fads.

This specific event in her life was a ferry ride along North Carolina’s Outer Banks. The year was 1951, and Lib was on vacation with her aunts and uncle. They visited the Elizabethan Gardens, the Wright Brothers Memorial, and saw “The Lost Colony” at the Waterside Theater with Andy Griffith starring as Sir Walter Raleigh. “He was a high school drama teacher and this was his summer job, but it was his big step to fame,” says Lib.

“I had just graduated college when this was taken. I was a home economics major which included a lot of art and costume design. Here I am wearing a yellow pique dress which I made to wear at work. I think the fabric flowers on my dress were a bunch of violets. I wore a baseball hat style with a narrow brim on the ferry to keep my hair in place.” -Lib McPherson

Some people are born to break rules. On her first day back from maternity leave after having her baby at age 24, FOF Robin Mizrahi wore hot pants, fishnet tights and high heels.

Today, at age 51, she’s toned it down, but she’s still not afraid to challenge conventions. “I go against what’s expected. If everyone is wearing narrow, I go the opposite extreme,” says Robin.

“When I was younger, I wore all one designer—head to toe. I would wear all Azzedine Alaia. When Gaultier did the Russian thing I had to have all Gaultier. (It was me and Janet Jackson wearing that look.) Everything was very body conscious, because that was the style: Big hair and boobies that looked like torpedoes, thanks to Madonna. And shoulder pads! Now I’m a lot less showy. There comes a point when you don’t have to do that anymore.” –FOF Robin Mizrahi

Sometimes we get it right the first time. FOF Janet Hankinson nailed her style early on and has stayed true to it ever since. Growing up in London in the “swinging 60s” and later settling in Berkeley, CA, Janet’s wardrobe reflected her free spirit and artistic edge.

“I have a photograph of myself when I was traveling through Spain with my father at fifteen. I’m wearing a beautiful skirt with a Liberty print–you know, the Liberty store in London–a plain white top, a large bangle on my wrist and Ray Bans. My style hasn’t really changed since then. I still like bright patterns mixed with solid colors. I’m not particularly feminine, rather, kind of bold and sort of striking.” -Janet Hankinson

“I looked like a total circus act,” said FOF Marian McEvoy about her style in her twenties. “When you’re 20-something you can do anything. What do you have to lose? I was a clotheshorse… wearing eight hats, 40 handbags, sweaters with three arms, a pant that was a skirt but it was a short, whatever.”

Marian may think she crossed the line from avant-garde to avant-gaudy, but her style impressed the editors at Women’s Wear Daily. They made her their Paris fashion correspondent when she was in her early 20s. She stayed in the city of lights for 17 years working on assignments for the International Herald Tribune, French Vogue, and the Sunday Times of London. In the late 80s she was named editor-in-chief of Elle Decor and House Beautiful in the U.S.

Today, Marian is more ringmaster than “circus act.” She steals the show with her tailored but creative personal style.

“I was 22, I was adorable and I could get away with it.” Marion says. “I don’t want to experiment now. I want to look really good, as beautiful as I can, I want to be able to move in my clothes and I want people not to point at my skirt but to point at me. Look at Marion, not look at that skirt.” -Marian McEvoy