Sheryl Crow is one of those timeless, consistent talents who has always felt comfortable with her own classic image. I find it intriguing and refreshing that she has never bowed to the pressures the music industry often puts on people to look a certain way. Sheryl's look is always modern but never trendy, so whenever I work with her, I know it's important to give her a look that's appropriate for the event yet true to her image.
This is the case whenever you're working with a celebrity client: In addition to considering her personal image, you also have to take into account the nature of the event and the audience. You have to be in tune with the other stylists so that everything—clothes, hair, makeup—is in sync. And most importantly, you have to be ready and able to redirect your creative energy and switch gears on a dime. It's one thing to have a strong idea of what you think will work well, and it's quite another to know when not to do what you had in your head, once you see the clothes, the hair, the accessories. Until I talk to the stylists, my ideas are just that, and you can't be married to ideas. You need to be creative and flexible.
For Sheryl's look in the photograph here, her hairstylist and I took our inspiration from her glamorous outfit, which had a retro feel to it. Sheryl looks great with a smokey eye, because she has light eyes. But instead of the typically retro, very 40s approach, I made it more modern by going smokey all the way around, yet when you look at the image it still feels classic. Her hair also has a gorgeous retro feel.
No matter what your level of experience, in order to create classic looks, it's absolutely important to be familiar with different eras and their respective icons. You have to know what's meant by a 1970s Studio 54 look or a 1930s Josephine Baker look. My advice is to spend a day in a bookstore poring over photography books and old Hollywood books—you'll find everything from 50 years of Playboy covers to a history of Vogue. Google celebrity names and you'll be amazed at the volumes of photography you'll find. It's part of our job to be familiar with what artists before us did so we can do it as well, and make it our own. Your interpretation doesn't have to be literal; you just want options for going beyond the typical approach. If your client references an iconic actress, she'll truly appreciate that you actually know what a Mia Farrow pixie haircut looks like, and you won't feel inadequate.
When working with your own clients, always take into consideration what her lifestyle is, not just what you think is going to look best on her. Be smart enough to know what is going to be a home run in every way, whether it's for a wedding or a prom or something she can do in five minutes every day. Meeting her needs will make her happy, make your job easier and make you look better.