My favorite artist from the 20s would be John Held. He did cartoon drawings of guys with their hair parted in the middle and slicked down, guys in Racoon coats and girls dressed as Flappers. It was also during prohibition so there was what was called "Bathtub Gin" or homemade alcohol. Here is one of them.
This forum is making me crazy this morning. First it wouldn't move from the post, then it didn't accept the attachment and now I see it has double posted. Grrr. Let's try this again.
With the 20s Art Deco is the way to go!!!
You may also want to check out Alec Baldwins characters office in the Aviator.
Or the Ziegfeld follies or Ziegfeld girls.
HTH be sure to post when you finish.
One of my favorite cakes is a Sweet 16 cake by BrandisBaked that features some burlesque girls. Something similar with flapper/burlesque girls might be really cute.........just an idea! Here's a link to Brandi's cake, if you're interested
http://cakecentral.com/modules.php?name=gallery&file=displayimage&pid=108551
And here is an example of a really wonderful art deco cakes. Art deco sculpture had many triangle and diamond shapes.
I am really loving the triangles on the bottom. I am familiar with the 20's and art deco-I just need an idea to put to a cake 
I'm stumped!!!
And here is an example of a really wonderful art deco cakes. Art deco sculpture had many triangle and diamond shapes.
I am really loving the triangles on the bottom. I am familiar with the 20's and art deco-I just need an idea to put to a cake I'm stumped!!!
You could make the triangles or diamonds of gumpaste, just make a pattern of lightweight cardboard. Dry the pieces and paint them silver, gold, bronze or a combination with luster dust thinned with alcohol. Let them dry and attach with royal icing. Build them in layers on top of one another. How you would use ths in a graduation would be up to you, you could do something similar to the photo and just use a mortarboard cap, a graduation figurine or even a stack of small books as the topper.
Here is a link to Ask Ginka. I use them a lot for theme ideas. Scroll down almost to the bottom for "Cakes" and click on each bakery, you may find something interesting there you could use.
http://www.askginka.com/themes/1920theme.htm
I stumbled across this in the gallery, and I remembered your post. This is such a great 20's cake by sugarflowers:
http://cakecentral.com/modules.php?name=gallery&file=displayimage&pid=66241
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