If you like something, go for it!
It took me a long time to be comfortable enough with my body and myself to wear the style I enjoy. [I'm a bit of an introvert myself.] Until then, I wore a lot of baggy clothing myself!
One thing you could do is go shopping either with a good friend or alone. You don't have to buy anything, but just try on different things and see how you like them. [For the hair color thing, you could perhaps try on different wigs? Or maybe temporary dye like what they have for Halloween? That way, if you don't like it, it'll come out really easily, and if you -do- like it, you can make it more permanent after that.]
Just some advice from someone who completely understands!