Follow the rules. Get off probation.
Most commuters have a jacket or polo to commute in. Almost everyone I know has jackets to do walk arounds in for winter. I am not wearing it with my hat.
If its pouring or -20 then yeah, I’m wearing it outside. I am not the least bit worried about getting in trouble wearing it on the ramp in rain or snow.
Good judgment for safety still prevails with all the chief pilots I have talked to. I have seen guys get told to wear their hats by the CPO, but no paperwork was done.