flappers, fedoras; also, my tenth high-school reunion

I haven't updated in a while.
I'm going to start off with a question.
Oct 8th is the photo shoot for the August calendar page for my roller derby league's pinup calendar. (We figured it would make good merch.)
We split the calendar up by the simple mechanism that each month would feature the girls born in that month. So I'm in August with Mia Mauler, Sissy Fit, and Lizzie McFighter. Me and Mia are big girls, though she's less, er, chubby and more, er, muscular (with huge shoulders), and Lizzie and Sissy are both skeletal on the thin side.
The theme for our month is Flappers and Gangsters.
I mentally Google-image-searched the 20s and realized immediately: This is not a historical period I can pull off. Given that I can't convincingly dress as a man, and also the "flappers" of that era wore long straight corsets to give themselves no breasts or hips, so they could achieve a fashionable silhouette.
So I've decided to dress totally unconvincingly in drag and see how it goes. Mia's dressing as a gangster too—I admit I can't see her in a flapper dress either.
But that means I need a gangster costume.
Where the heck can I buy at least a fedora, at most a reasonable men's suit that would be tailored (or tailorable) to a woman's shape? I have a gray trousers-and-vest set that I could wear, but I don't know how well it would work.

At least I don't need shoes, as we're probably doing it on skates…
If we do this right the two skinny girls will make great flappers, but I don't know how well we're coordinating. I don't recall precisely how we chose the theme, but both Sissy and Lizzie would look fabulous as flappers.

I could invest some effort into this and have a good Halloween costume too…

Sigh. Anyway.
( Not a coherent write-up-- just some ruminations. )