I love pieces that can be worn in a variety of ways; they minimize your investment in something new and add multiple new looks to your closet, in a word: brilliant! Check out this dress by Amanda Uprichard below as an example. I styled it three ways: as a top with denim and boots, as a standalone dress, and as a dress underneath a brightly colored jacket (hot pink in my case!) Links on where to shop each piece are available at the bottom of this post.
YSL boots (similar)
Amanda Uprichard dress (mine is not worn off the shoulder as shown in link)
Coach Jacket (similar by Neiman Marcus + cheaper!)