Speaking from personal experience, you have to be extremely careful when cutting hair really short, especially wavy or curly. I went from almost waist length hair to a pixie/crop, and hated it. Not that I hate short hair. I LOVE short hair especially messy pixie cuts, but my face was too long, my hair shrank too much because of my wave/curl(though it was too short to look wavy it shrank almost an inch), and she cut it too short. It was awful.. and my best friend and her mom thought I look kind of like a ferret(the cut brought a little too much attention to my big, round eyes). XD
But that aside, if you're dead set on a shorter style, then I would definitely recomend something I little longer then those. You have a longer face, and those cuts wouldn't be flattering. The would make your face look longer and more narrow. http://marianrothschild.com/wp-conte...e-haircut1.jpg
I would get something at least this longer, maybe a little longer to be on the safe side. You can always cut off more later.
As far as growing out, it might poke out in some places(might not), but for the most part it should look the same way it does now once you grow it out. I had a pixie cut about 3-4 years ago, and aside from that akward phase of being between just above your shoulders to just below, which everyone goes through who's had short hair that they're growing, My hair grew out quite nicely in the end. Trying to get it back to waist length right now.
I also love men's wear and suits, and wear them fairly often(if not more mens wear inspired clothing, vintagey type things), and I love your "shirt". I'm only 5'4" but the way I'm built(big bust small waist) I have a hard time finding dress that don't end up mcuh shorter then they should be.. hehe I imagine you would prefer a more low maintance hair care routine, but you might try going CG, especially before dying your hair(the healthier it is the better your colour will turn out). It should also help cut back on the frizz.
Oh goodness, that was a lot. I think I covered everything. ^^' Sorry about the length.