Welcome back!
Your use of the word Bob shows you've still been with us in spirit.
I would ask the hair stylist on their opinion, but if it's something you want to try I would say give it a go.I think there's some websites or apps where you can upload a picture of yourself and try different styles so that might give you an idea to work with.
Start slow and with baby steps with the weight gain. Small changes that are manageable rather than drastic diets.