I love the idea of a bike ride, to put yourself in perspective.

IMO, it is your hair and wear what makes you feel comfortable.

I had hair down to my waste until I was about 35, (I'm 52 now) then cut it to shoulder length. Have been there ever since. My hair is very wavy and when I had it short, it always felt like it looked like I rolled out of bed.

I'm on the fence on what to do with it now.