So I'm about half-way through this challenge, and I think this is the first time that I finally got around to wearing a dress, which was the main reason why I started this. Which proves the point that wearing a dress while looking casual is difficult, and also that it isn't too difficult to dress up wearing jeans :) To pull off this style though, especially in the winter time. I went with leggings to keep my legs warm and a dress shirt to keep my shoulders and upper body warm-though a jacket was needed for when I went outside. Though I was wearing a dress, since I did not wear heels, but rather boots and leggings, I did not look too dressy. Of course summer dresses aren't quite as formal anyhow, but perhaps that is the key. We shall see.
Outfit #18: Summer Dress, Boots, Leggings, Dark Grey Dress Shirt.