A: Always look clean no matter what your look is and always wear cool shoes that match the your style. Remember that being too comfortable may feel right but will look wrong.
A: Depends. Tan in the summer looks good, especially if you're a blond. Tan in the winter just looks out of place like you're trying too hard. So it all depends what skin color you are. Does it matter, I would say yes. Just know when to do it.
A: If you're tall wear long. If you're short wear short, or long will make you look shorter. Fair skin brown, dark skin black but this can work either way more a matter of taste.