Fortunately, I have short hair so unless it's a real hot day, helmet head isn't really too bad-- just have a brush stuck in the "trunk" for a little retaming.
As far as the makeup thing, if I'm gonna ride, I skip foundation, etc. Just do the eye thing and a little blush and good to go, no rubbing off in the helmet and I can go through a work day without looking like I just rolled out of bed...
What are you worried about your hair for? If you stay on your bike the whole time you'll never have to take off your helmet. As the guys have mentioned... if you want to look good and cruise, use the car. If you're THAT worried about your hair the easiest solution is to just pull it back. I prefer to french braid it for a more femy look when the helmet is off, but when it's time to put the helmet back on, back to a pony tail.
As for make-up... YUK! It makes my skin crawl just imagining having make-up on while riding. Your pores are going to enlarge because you're going to get warm and the helmet will rub that shit right in. One week later you'll be wishing you had stock in Clearasil. No thanks on the make-up.
If you're just going out for a ride, yeah, who really cares
But, sometimes (actually a lot of times) I also commute to work and have to deal with the public. At those times I have to care at least a little of how I look and don't want to be confused with a Harley Biker Momma Price I am willing to pay to find some way to get a ride in during a 12-13 hour work day-- at least it's a 40M roundtrip commute, that at times becomes 150miles to get home-- hee hee!