My setting is 1928/1929 pre-Black Chicago which according to my research, was a hot bed for speakeasies and gaming as well as having a variety of mobs. I've done a fair bit of looking into historical information of the past and I know that a German family in control would be a bit of a stretch, but there is a fight for control with a Irish group, so...
My questions are:
1) How taboo would it be for a woman to wear pants? I've found nothing so far, all I've found is discussions on sexual liberation and the rise of shorter skirts and more androgynous clothing.
2) What about fashion for men, I know the Zuit Suit is about a decade too advanced, but I'm looking for something similar in style - slick, tri-pieced, etc. And I'd like to use descriptive terms rather than just "suit", so anything would be helpful please.
3) Am I too early for cigarette girls?
4) Would an African-American entertainer, more than likely blues or early jazz, definitely female, be out of place in a mob owned lounge or bar? She would be out of the social circle of the men she's performing for, but she would clearly be aware of the fact she was performing in a speakeasy. Perhaps even be a favourite of theirs.
5) Okay, now for the tough question. My main character is first generation German-American, his father immigrated when he was around 15, but still fluently speaks the language and taught it to his son. I have ideas for when my character gets tired, or is in the throes of passion, he starts dropping his English, for his more comfortable first language of German. But he is also prone to German idioms, catchphrases, and the like.
What I'm looking for, which I could never ask my Oma, are:
a) German sex talk.
b) German slang and catch phrases, or expressions.
c) German insults and swear words.
Thins I have googled are: 1920s America, 1920s fashion, gangsters, German, German expressions, German curse words, flappers, Prohibition, cigarette girls, and pants (The wiki page is actually quite interesting).
ETA: I'm also looking for how Asian-Americans would be treated, having been born in America, but given xenophobia
Thanks in advance for all your help!
EDIT: I think I've gotten to everyone, thank you so much for all your help. I now have a better understanding of where to go with the character and the plot.