I wish I felt more comfortable without makeup, but I don't. I don't mind working out without it, but I otherwise wear at least some mineral foundation, mascara and blush. I'm very, very pale and even with makeup sometimes look a little lifeless. My dark hair and dark eye circles don't help. I hate foundation as a general rule, but I love the mineral makeup. It's easy to put on and doesn't smear off onto other things. Whatever makes you feel good about yourself is fine by me.
And as for the OP's original issue with women getting makeup on clothes: Even if you're careful, it sometimes happens, but makeup almost always comes off in the wash. If I buy something that has some kind of a stain on it, I usually just confirm with the store that I'll be able to return it. Or ask for a discount on it.
Live with intention. Walk to the edge. Listen hard. Practice wellness. Play with abandon. Laugh. Choose with no regret. Continue to learn. Appreciate your friends. Do what you love. Live as if this is all there is.
--Mary Anne Radmacher