My take is that if you are white, then be white and don't worry about getting color. If you get lucky and your skin darkens up, great. If not, oh well, God made you white, so embrace it.
I too wore hats a lot, even before going sly. Now that my head is shaved, I find them uncomfortable. Give it a couple of weeks if you aren't willing to commit to a full 30 days. I think you'll get more comfortable with it along with everyone else. It really only took me about a week before everyone just forgot that I used to have hair.