I never bra outside of the workplace. I will take measures to make ensure that my bralessness isn't obvious in certain situations (funeral, church etc) by wearing an outfit that conceals it somewhat . But I still refuse to bra outside of work...my girls need some unleashing time!
I USED TO always bra at work until recently. In my effort to become completely brafree, I'm phasing out my wearing even at the office. Now I wear one there when I have to (if the outfit makes it obvious) and don't whenever I can get away with it.
I plan on slowly cutting down on my wearing with the goal of eventually being 100% free. NOt only am I introducing brafreedom at work, but I have thrown out alot of my bras, and plan on never replacing the ones I own once they're worn etc. This way I have some sort of 'deadline' to be 100% free. When they're all gone, I won't even have the option of wearing one (thanks to Michaela for this suggestion way back when!)
Hey, as long as I have a bra around, I may chicken out at times and reach for the harness!