Years ago, when working in Georgia it was often an undertaking to carry off duty and concealed. In the early years, pretty much the only option was wearing jackets or leaving your shirttails pulled out for easy access. Then enter the tactical off-duty photographer-type vests, the ones with lots of pockets. Vests were all the rage but soon became identifiable as apparel for off-duty police officers trying to look cool. And please do not remind me of "fanny packs." Later the tactical equipment manufacturers came out with their concealed carry tactical shirts. These are great and I even have a few. But still there is a void; attire and attitudes need to match.
For veteran officers, there are a few of us who don't care or don't possess any fashion sense whatsoever. You know the old guys that when they walk across the room they make creaking sounds? They tend to wear Hawaiian shirts or sometimes bowling shirts. A few even spring for the Guayabera shirts, which are generally the same style but make far more fashion sense. All of these bigger, looser fitting shirts are comfortable and easily conceal your weapon. But they also speak volumes about the wearer, other than no fashion sense.
Dress Codes
When you attend training, especially training conferences, there are some rules. There are some departments that still require officers to wear duty uniforms or logo-bearing shirts to training classes, even those out of state. They believe in showing the flag whenever possible. Most request business casual for meetings. Kind of stiff regulation, I would say.
At most police conferences where officers are free to wear what they want, you'll still find the younger ones in tactical shirts and tac pants or jeans. There will be plenty of T-shirts that reek of personal vocational statements or product recognition. The baseball hats with "the crush" effect and sunglasses are still in vogue. The one major point to be made here is that most of us have worn uniforms all our professional lives, to include military service. So even when "off duty," we tend to still conform by wearing identifiable tactical wear. What I find important is that sometimes we just want to be ourselves and relax.