My favorite look for what i consider old hollywood glamour:
Eyes: Shroom on lid (#242 brush), Cork in crease (224), Mylar to highlight (224), a little Goldmine on the outer corners (224), tightlined with Brun (#263), Blacktrack fluidline (209). Benefit Bad Gal Mascara on outer 2/3 of lashes.
Brow: Brun shadow applied with #266 brush
Cheeks: Frankly Scarlet blush lightly applied to the cheeks
Lips: Ruby Woo lipstick
You might want to check out besamecosmetics.com. Their line is all about retro makeup. I havent tried any of their products, but on the website, under Vintage looks, they have some helpful how to's on how to apply makeup for a 1920's, 30's, 40's, or 50' look.