Above all, wear what you feel comfortable wearing. If your comfort level is up, you'll be able to rock anything, although, as has already been said, you do want to at least dress in context. If you haven't already, check out thrift stores. I've found that a great way to try out new styles for really short money. If you find a style, or individual piece, that you love, THEN you can go and pay full boat for a properly fitted item. Experiment. Enjoy.