I think it depends. I've been interested in an evening Boy, but of course I wouldn't want it in the new Medium size. The old medium might also look weird with a dress and high heels. It just depends on the style of the bag and how you want to use it. The new Medium would look pretty cool as a day bag or shopping, but the super fancy styles (glitter, patent) might make it look flashy. It's all just up to your tastes.