If your clothes fit, you’re on the right track. Now, you have to check your proportions. You never want to wear too many items that feature the same amount of volume. “If you have loose pants on, balance it out with a top that is not too big. The same for if you have on a loose fitting top; you should wear it with leggings or fitted jeans,” says McGary. When you contrast proportions, your outfit has a sense of balance, which is the ultimate goal for any casual cool look.