I’m not a man, I’m a girl, but I can relate. My parents wouldnt let me wear anything from the mens section. Even Unisex things like plain t shirts and sweaters.

Now I like to wear some pretty funky clothes. Family doesn’t approve but I’ve noticed that my most “out there” items get the most compliments.

My assumption is that most people don’t like it, but then the people that do are just so excited to see something unique that they also like. So they kinda wanna show solidarity I guess? That yeah it’s weird and maybe most people don’t like it/makes them uncomfortable, but you like it and I like it so we’re more on the same wave length than most people. Makes you (the wearer) easier to approach because you share a special bond.

For example. I have a fish shaped purse. It is objectively ugly. I love it. If I saw someone with the same purse I would flip out and tell them. If I saw someone with something equally out there I would feel like I could approach them easily and say I like it, because in a way they’re kinda like me.