Just so everyone has access to the same information I've based some of Lucre's foundations on, there's a significant disparity between what most modern people think of as being permitted during the 20s and what actually went on. Initially I had intended to make my club a very Gatsby-esque fancy speakseasy. Lots of women in flapper dresses and tuxedoed guests and all the things that immediately come to mind with the roaring twenties, but while doing research on what speakeasies were like I stumbled upon mention of the "pansy craze" and after looking into things a bit discovered a really interesting turn-about.
Our characters exist in a period when LGBT entertainers are some of the most popular nightlife attractions available. Drag Balls, female impersonators, and cross-dressed singers are going to be a hot ticket for the next decade or so, only really falling out of favor when prohibition ends and the legal push to move liquor sales to 'upstanding vendors' removes patrons from the less than legal bars where LGBT nightlife could openly flourish. For a few more years Gene Malin is headlining performances in New York, flouncing across the stage on Broadway, and getting drag parts in films. Gladys Bentley will be dressed in menswear and openly flirting with her female patrons in Harlem Blues clubs for another decade and they're just some of the ones that make it into the news. That doesn't even begin to touch on 'the black and tan' clubs and how the mindset on racial diversity and popularity of jazz and blues is starting to affect views on what constitutes normal for the average American.
It's a very interesting time, and unfortunately most of the progress made during that era will be lost in the moral panic that starts to take hold around 1936 in regards to 'sex fiends,' but for at least a couple years we get to enjoy a much more permissive atmosphere. All of which ties together to let me add that if Fey wants to come sing some night in the most glamorous tux Matthias can afford for her I can almost guarantee great returns for all parties. ^-^
Spoiler for references for the scholastically curious: (Highlight or hover over the text to view)
The Pansy Craze:
https://www.pinknews.co.uk/201...-of-lgbtq-nightlife/
Normalization of homosexuality in 1920s Chicago:
https://www.chicagomag.com/Chi...er-2005/The-Gay-30S/
Drag balls and female impersonator popularity:
http://outhistory.org/exhibits...le/part-2/drag-balls
http://www.loftgaycenter.org/s...ime_at_the_speakeasy
Prevalence of LGBT events in the 20s:
https://www.history.com/news/g...twenties-prohibition
Scholastic essay on the topic:
https://www.apa.org/pi/lgbt/resources/history