While there are "rules" for dressing and "best practices" to achieve the most desired looks for your wardrobe at the end of the day do something that makes you feel good. If you want to wear leggings, everyday do it. If you want to wear a purple chicken suit, do it. But just make sure that it is because it makes you feel fabulous and not that you feel lousy, so you wave your hands of TRYING to feel great. Because one thing, I have learned in the years that I have been in retail, helping people to shop.... We all have some self loathing from time to time. If you just really feel like you don't know what looks good, enlist a friend, or store stylist (be careful, if they are commission based). But the bottom line? Find ways to make yourself feel great. Life is to freaking short not to.