Venatore done a similar mod, just had to change a cfg file iirc, just check out "Venatores Drive through", it was called "Random Crew Headdress", At the
start of a new career you can have all the crew with headdress & as new recruits are transferred via SH3 Commander these will randomly have headdress, after half dozen patrols or so you will find most of the men have headdress & some don't:

I have an updated version of this file if you want I can upload it.