I'm definitely going against the grain here, but as someone who has been known to wear a skirt or dress now and then
when I get all dolled up, I want to look girlie - and that means tucking the boys up inside and my dick against my ass. It's pretty hard to wear nice panties with the whole package hanging out, and the bulge at the front of your skirt isn't very femme.
Now the bedroom is another matter - time to do some showing off. :D That's when you let it hang out and show.