Originally Posted by lostfairy
He gets frustrated and says he's a guy and doesn't know and whatever I pick will look good. Honestly, I know this, but the questions come from my insecurities about the situation I'm going into.
He's giving you a straight-up honest answer. He IS a guy, and he probably really DOESN'T know, and whatever you pick really WILL look good to him.
So let him off the hook on this one, and either don't ask him what he thinks about the fashion choices, or ask him for a little reassurance, to help you deal directly with the insecurity issues. I'll bet he'd be really good at that.