What about pieces from the Jitterbug trunk? Or that might be too early, or too late. 40-50's I think of the poodle skirts
Polka dots were really popular in the 50s, I think? As were poodle skirts, so I agree with what said. That would also possibly make it more obvious what you're trying to go for. :) Also maybe jazz it up with a floral item in the hair, or just a small clip?