Founder of cosmetics line Lipstick Queen
"At around 17, I had an aha style moment: I looked—and felt—better when I emulated the style of the 1940s than when I tried to achieve a modern look, which at the time was Debbie Gibson and Pat Benatar. My pale skin and sharp profile make me look more like someone out of an old Hollywood movie. So I stopped trying to get a tan and started experimenting with red lipstick. My search for the perfect deep matte shade inspired me to start my first company at 18. Fine-tuning my style over these past 20 years has been a trial-and-error process of understanding what really works for me. One thing I figured out pretty quickly: When your overall aesthetic is vintage, you have to beware of getting costumey. So I always mix it up. If I'm wearing a very sweet floral dress, I add a studded belt; if I have a full-skirted silhouette, I skip the delicate handbag. Over time I've learned to strike the right balance—I hope!"
Signature Style Rule #2. Don't make things too hard. "Great style enhances your life—it shouldn't rule you," says King. She spent years glued to the Weather Channel, terrified of rain. "I was a slave to my blow-outs. After I'd found the makeup and clothes that worked for me, it was still another ten years before I embraced my curls."