Sounds like you're still a kid at heart. I've got a 2yr old and I immensely enjoy playing these sorts of games with him. My wife always jokes that I'm using the sandbox more than him, she even snapped a couple of pics of me playing alone in there.
What kind of clothes are you talking about? A skirt on a man is still pretty courageous, but if you're talking about a pink shirt just go for it. You'll not be judged.