I wear skirts and dresses with biking shorts underneath. they are comfortable, cool and with the shorts, no accidental over exposures during a breezy period.
I wear makeup as well, I like having nice photos and I like the way I look with makeup. Unlike your wife I don't call people names who choose not to wear makeup. If I were you I'd worry less about how other people would judge you and maybe advise your wife it isn't very nice to judge other people.
Also if she looks like a circus clown with makeup on, she's doing it wrong.
She's doing it wrong.