Did you know high heels were originally made for rich men? It was a symbol of status way back when

Especially if you're wearing them underneath your jeans most people don't notice shoes unless they're looking on the floor and even then they're hardly paying attention. I guess my advice is to do a short trip in them. Like a grocery store visit. And then ease yourself into being comfortable wearing them for longer and longer times in public. I'm glad you're giving it a shot though It's frustrating when no one sees it as strange for girls to be wearing guys clothes but the moment a guy looks more feminine he gets harassed. I'm glad you're pushing yourself to be comfortable and breaking a norm at the same time! Way to go!!

Best of luck! I'm rooting for you!