Stephanie Stokes Oliver,
Editor and author

I never considered myself beautiful or even pretty, so I chose clothes and makeup I thought would make me look cute. I did think of myself as a person with a strong sense of style..

About every three years I give myself a makeover. In my switch from magazine editor to Web editor and author, my style has changed from corporate power suits to 'work-at-home whatever.' Now that I'm in the burbs, I live in wool knits, jersey knits, any kind of knits. For publishing lunches and my book tours, though, I slip back into suits, maybe leather pants, suede jackets, anything that wraps—and the higher, less comfortable heels of my past urban life.

Kitty Hawks,
Interior designer

Knowing who I am comes from an internal rather than external image. The more secure I am in that image, the less I need to manipulate it.

At this point, my style is the result of accepting what time has wrought. No matter what you do, aging happens. You get lines around your eyes. Your features become less defined. So I use makeup to define them—to darken my lashes, add color to my cheeks.

To me, the good news came with turning 40—no, 50—because that's when I knew exactly how I wanted to look. When I was unsure of myself, I changed my style all the time. And then when I finally got it right, I settled happily into a kind of comfortable consistency.

Lisa Airan,

My approach to style starts with the mind. In order to be truly stylish, one needs to have a certain fearlessness and individuality. I don't follow trends. If I like how something looks, I buy it. I would say my overall style is feminine and discreet—and always with a twist. For example, if I were wearing something basic or very minimal, I would choose a bag with an interesting color or texture.

I became a dermatologist because I love the field and love helping women feel more confident, enhancing their beauty. But my work has also made me understand that people need to learn that beauty and style can come from inside. When you have a positive sense of yourself, you radiate and people are attracted to you.

Jenny Lumet,

A few years ago I started wearing things that pleased me. I didn't think, 'Can you see my butt?' I just stopped having those kinds of unhealthy thoughts. I met my husband and we had a baby. That was the best thing for me. Having others (including my dog) to be responsible for made me feel free: I wasn't focused on only me, me, me.

I was once looking for whatever it was that would make me okay for everyone else and realized that there is no such thing. As an actress I felt constantly evaluated, but I realize that I've been in a position to challenge the perceptions of what being black is. When there is no road, you make a road.