I have a strong preference for the first shoe . I don ' t really like the peep toe and the patent leather of the second shoe . One might be able to argue that the peep toe and patent give it kind of a vintage look , but I think that they actually look a little dated . The first shoe is much more of an invisible shoe . It ' s shape and material suits current trends without being trendy and they can highlight the dress without drawing any attention away from it . The only thing that kind of makes me raise my eyebrow is that you said you want to wear this outfit to school . What kind of school ? I can ' t think of any school where it ' s situationally appropriate to wear that dress and stiletto heels . You will look like you are dressed up to go to a party .