Your clothes should be an extension of your personality. What kind of image do you want to put forth to the world? Are you a tailored, classic professional? Are you quirky and artistic? Flirty and romantic? Trendy and modern?
Use your look to show the world what you're made of. You'll feel more comfortable in clothes that are truly "you." If you're more the quirky and artistic type, you probably won't feel comfortable in classic, tailored clothes. And if you're into the tailored and classic look, you'll probably feel a bit out of sorts in trendy outfits.
Select pieces that represent your personality best -- peasant skirts, tailored button-down shirts and pencil skirts, ruffled blouses, platform shoes, pinstripes, polka dots. Whatever makes you, you!