Wotta,
These days, Stn Cdrs have so little actual power, the only things they can actually do anything about are 'hats on/off' and 'designated car-parking spaces'. Give him a break!
Admittedly, its a bit sad and hardly 'big picture' stuff, as you quite rightly point out and yes, there are better and more effective ways to get people to have a bit of pride in their appearance but how else is he going to make his mark and get promoted? Some of the best and up-beat units I have seen were united in hatred of their @rse of a Sqn Boss/Stn Cdr - who then, regrettably, got promoted....aargh!
However, as others have said, wearing a hat is not a difficult thing to do. So, unless you want to make a bad name for yourself, do as he says, paste a happy grin to your face and keep your powder dry for the big issues. If the Stn Cdr gets those right, however, maybe he's not so bad after all? Although, his apparent lack of focus does not bode well for ISK.
In the meantime, always remember RULE 1 - DON'T GET CAUGHT!!!!!
