Simplest thing to do for your own use is use the scale dials and parent the hair to the characters head for both prop and figure hair. If it is a still render, you are never going to see poke thru on the back side from the camera view. Don't do like I did early on and get trapped up in trying to make a hair fit perfectly only to realize the part you were fussing over was 180 degrees away from on never seen by the camera.

Animations whole different issue.
Clothes, I use WW2 and on certain cloth X Dresser.

Gary

"Those who lose themselves in a passion lose less than those who lose their passion"