What is the most embarrassing thing you have ever worn?

I've always been classy with my wardrobe. I've had an emo phase but we pretend that never happened.

Herman's Hermits tee shirt.

Too many to name. I grew up very poor. Won't wont relive that here. Then again in my 20s I didn't grow up with anyone to teach me about style or how clothes fit my particular body so I made a few bad choices again.