Well, who's the best looking lady? I've always thought Jack Lemmon pulls off womanly style the best. From the top is Tony Curtis & Jack Lemmon in Some Like It Hot, next is The Three Stooges in one of their many girl costumes, then we have Lionel Barrymore as an elderly woman, and finally Bing Crosby in a stunning gown! I know there's more but I can't think of them, so these will have to do for now. I have to say, I love Tony Curtis's travel case!
Personally I don't think that 1920's swimsuits are extremely flattering to the figure, but at the same time I think they're really cute! It's like wearing a long wool tank top - comfy until you get into the water, and then it becomes 10x as heavy! Above is a photo of Marilyn Monroe wearing a 1920's swimsuit while filming "Some Like It Hot".