As I've gotten older, I've started to recognize the importance of fit and tailoring. This is especially important with vintage clothes, as they all have very specific fits and are meant to work with your body in a very particular way, creating a very particular kind of silhouette. The way something fits can make a big difference - even if you're wearing something fabulous, if the fit is off, it's not going to work quite as well.
Anyway, the young woman on the left looks very cute, and I like her sunglasses/hair/lipstick combination, all of which are very bold and simple and work with the strong graphics of her 50's style dress, which is from Anthroplogie a little while back (they still can make a cute thing occasionally.) But I do think the whole look would be better if she went to a tailor and had the sides of her dress taken in under the arms, creating a tighter fitting bodice. (Enlarge the pic to see what I mean.)She still looks fab and all, but if you're going to spend the money on a dress at Anthropologie, it's definitely worth it to kick in another $8 or so to make the fit perfect. Sometimes the store will even do it for you.