I aint picky about what I wear, but it helps to have a friend that likes to dress up. She will get you to wear all those nice clothes after beating you with a leg of lamb.
It also helps to NOT BE IN A STABLE RELATIONSHIP. When your comfortable with someone you truley care for, you won't be motivated to look cute. (because frankly you dont care anymore!)
Some girls always like to look cute, to make herself feel better, but those of us that are comfortable with our bodies often don't care what others think.
Tips, when you buy what you like to wear, (ie. hoodies, jeans, shoes, hats) Buy things that make you look good. Don't just buy it because it's on sale, but buy it because your attracted to it, you like how it fits, and you also think you look damn sexy in it.
Let me reiterate: BECAUSE YOU FEEL DAMN SEXY IN IT (that is the most important part of dressing, you want to feel GOOD about yourself!)
That is just about the hardest thing to do, but when you put some time and money into it, the outcome is worth it!!!