Man loses job. Frustrated trying to find another job, he disguises himself as a woman and lands a job. In this case, the job lost and found is that of an airline pilot. (I would have preferred airline steward-to-stewardess, but that's just my fantasy!)
This is the plot of a 2012 Swedish film titled Cockpit, which flew under my radar until I came across the trailer for the film on YouTube. Actor Jonas Karlsson’s femulation is presentable, at least in the trailer and handful of still images I’ve seen.
Wearing Ann Taylor.
Actor Jonas Karlsson in the 2012 Swedish film, Cockpit.