Where should I wear red lipstick?

Wear it on your forehead. When I was a boy, painting my face for war or games was part of the fun. When I didn't have face paint, make-up worked. I didn't call it make-up. I called it war paint.

Context matters. I don't really know anything about style or fashion. But I do know that you have to be comfortable. Try to coordinate colors with your outfits whatever that means. My wife hates it when I pick out my own clothes for the day. She also was wary of sending me shopping for her make-up. The poor sales clerk must have wasted hundreds of dollars worth of product trying to match the color on the paper my wife sent with me. Also make-up has a shelf life. It get old and dangerous. Make-up should not be shared. You really can get sick.

On your lips.

Wherever you want! Go for it