If you need to wear a cocktail dress with flats, I am here for you. From foot ailments and sprained ankles to rocky terrain and a general intolerance for discomfort, many of my clients want dressy flats (aka evening flats) for their party looks. We all love a high heel, but you can in fact wear a cocktail dress with flats and still achieve a slim silhouette. The key to pulling off a cocktail dress with evening flats is the dress length - it either needs to be a maxi dress or a mini dress.