You might have noticed that I almost always wear a jacket or cardigan (in fact that is most of what I bought as far as new fall clothes). I just feel like they are the quickest way to change up your outfit and to transition it for a new season/new climate. Here is one dress that I have styled to wear all year round:
Dress: Royal and Reese (sold out, similar here and here)
Looks 1 and 2: Kut from the Kloth Jean Jacket, Royal and Reese Wedges
Look 3: Royal and Reese Cardigan; Old Navy Black Booties (similar here)
Looks 4 and 5: Target Military Jacket (similar here); LOFT Wedges (similar here); Old Navy Booties.
Chic on the Cheap 