I have no conceptual problem as a cishet man with wearing skirts, but I’ve worn drag on stage in high school and it was sort of hard to stop flashing people my underwear at various points and that would be all I would think about if I wore a skirt now.
I have no conceptual problem as a cishet man with wearing skirts, but I’ve worn drag on stage in high school and it was sort of hard to stop flashing people my underwear at various points and that would be all I would think about if I wore a skirt now.
You could go with the athletic shorts under the skirt, still a lot of airflow but no risk of flashing.
Just wear a nice snug pencil skirt: no chance of flashing your knickers and it will look great with your heels.
That doesn’t sound breezy and comfortable.