Not sure if bug, oversight, or if I'm missing an inclination or something, but...
After unlocking River Rat management and going straight to topless outfit (because what else?), the following takes place:
-Clock in
-Get told to put on Uniform
-Put on Topless Uniform
-"You can't go out like this! (You're not wearing a top.)"
(And for the record in case it changes something, I'm pretty sure I have every Exhibitionist inclination; Cautious, Lewd, Proud, and Helpless)