Wow! Lots of replies. Thanks everyone.
My hair was waaay longer than this when I first started working for the company (almost halfway down my shoulder blades). I got it cut short (about 1/2 long) and this length is almost 10-11 months of growth.
With luck I'm hoping to start seeing a therapist in the next few months and maybe (hopefully) low dose hrt so I can start a stealth transition so I'll just keep growing it out and at some point get it trimmed but keep it long.
I'll give the bobby pins a shot and see how it goes. I'm reluctant to use hair spray because the less flammable stuff I wear the better and I would probably require a ton of it.
I've never considered curls, but I'll experiment sometime over a weekend when I have a full weekend and see what develops.

Thanks again for all the replies, I've got some stuff to experiment with.