Occupation: Designer at Rachel Roy

The stunning Rachel Roy started out her career in New York City as a stylist and then took the helm of Creative Director at Rocawear. Eventually in 2005, she would launch her signature brand, Rachel Roy, which showed the world what she really had up her tailored sleeves. Rachel Roy's personal style and design represents who she is; an independent and powerful woman that isn't afraid of her femininity. It comes as no surprise that icons like Michelle Obama and Diane Sawyer are drawn to her collections.