I am convinced that you actually can never go wrong with a simple black dress. It has quickly become one of my go to pieces because it's versatility (not to mention it's SO comfortable). You can wear it by itself for a casual day look, and easily dress it up for dinner or a night out. I suggest finding one with minimal detail, so that it can be worn different ways! For something like this, you don't need to drain your bank account. I got mine at GAP on sale! 

Black Dress: GAP | Bag: Hobo | Jacket: Madewell | Hat: True Religion | Brass Cuffs: Branded | Bandana: Madewell

Photos by Bethany Long