I'm not much of a "dress" person, I'm comfortable with jeans and shirts, and only wear a dress if I want to. To make myself feel better, I follow my heart.
I think first and foremost, you have to feel more confident about yourself. For me, it's accepting the way you look that will make you feel better about yourself. Regardless of what you wear, it's the mindset of a confident person that will let you shine. Remember, feeling good about yourself starts from the inside. So love yourself and you will look good, whether you're wearing a shirt, jeans or a dress.