Clothes shouldn't be about impressing others; they should be about improving how you feel about yourself. Dress in whatever fashion suits your attitude and style best, but just remember the person you're dressing to impress is yourself.
You rarely see confident men dressed poorly. Clothes reflect how we feel about ourselves - and confident men know and apply this logic. If you want to think and feel good about yourself, your outfit should mirror your intentions. And, wearing clothes that make you feel good, no matter what style they are, will instantly improve your confidence.