my mom got her first tat at 41. she was already a grandma. seriously. you are NEVER too old. if you want tats and piercings, go for it!
dark brunettes CAN wear pastel pink hair. case in point: me. I've done it as recently as this spring. there are even temporary ways to do it.
I also love the menswear shoes and legwarmers but wouldn't pull it off. I also LOVE fedoras, whether casual straw or dressier felt/flannel. but I just don't think I'm a "hat" person. my H loves baseball caps on me, so maybe I should try fedoras. I'd feel like I was trying too hard with them.