Dress from ASOS for $110, Hairband from Newlook for €6.99
For the day I would wear a quilted cross body bag and at night go for a beaded box clutch like the one above. If you want to go all out you can wear a beaded headband that wraps around your forehead or you can wear a statement necklace if you want to play it cool.
In the 1920's red lips were popular, among raspberry and pink colors. Darker red lips were more prominent than the cherry red lips in the 1930's and 40's. Smokey eyes with red lips were quite popular but today that is a "bit much" so I would go with more of a neutral eye.
Would you create a similar look for this fall/winter?