"I work in a youthful, creative business," Barbara Newman, 55, explains. "I know I dress too young, but I don’t know how to choose things that are more sophisticated without feeling like I’ve lost my sense of self." Gunn instructs Newman to limit the prints, try fitted tops and look for "jacket alternatives" that are stylish but not stuffy. "You can look youthful," he says, "but still have polish."