It's quite sad when you're told you aren't cool by your own family member. It happened to me a few days ago when my dad picked up my son from my office building.
Like any other Friday, I decided to wear a golf shirt with jeans. The golf shirt I decided to were that Friday has three buttons, and I had buttoned the bottom two.
After settling my son in the backseat, my dad looked at me and said, "Unbutton your top button. You look like a nerd." This comes from a university professor who use to teach a whole class with his pant cuff under his sock.
"Thanks dad," I responded refraining myself from saying some sarcastic remark in public in front of my office building.