Three dresses, or a romper of such, I recommend grabbing a flowy dress for brunches and casual outings and a more classy fitted dress for your nightly functions out in town. I usually, for this pack, the five-year-old black dress that I refuse to wear a bra with. Three pairs of shoes as well. My head turns towards my white low-top Converse, Birkenstocks, and fancy sandals to pair with our fancy five-year-old black dress, of course.