I haven't started transitioning, and currently I wear cargo shorts despite all the recent ridicule those have started getting. I feel like I won't have much trouble getting used to carrying a bag, considering I already know I could use the space. I'll probably have a basic little canvas thing or whatever. I'm well in touch with my feminine side, and it's a pretty trashy little thing. As long as I can put pins on my bag and money inside it, I'll be happy.