Hi, Jessica, sounds awfully familiar, especially the wife.
I'm working on inducing male fail right now. I've been wearing my Gloria Vanderbilt jeans almost exclusively for a few months now, with the tags removed ("Why does it say 'Amanda' in your jeans?"), and a cotton tank on top to hold things down, covered by a loose, untucked polo shirt. Now, I'm not wearing the tank, but I am wearing a tucked in thin polo shirt. 34B on top, and the headlights are on... 28" waist, 36" hips.
I don't think I look like a typical 60-something male except for the shiny head. Baseball cap over that... And this waterproof eyeliner and mascara is really hard to get completely off, y'know?
If that doesn't trigger a discussion I'll start ignoring the house rule about not presenting female around the family. Oh, I don't look like Daddy any more? Huh. Must be a reason...