This season you're going to see shift dresses everywhere! I absolutely love this silhouette because it looks good on every body type. Find one with a geometric print that is vertical though the center of the body. This will make you look thinner and taller!
The weather is changing at the drop of a hat right now so I suggest layering this dress with a blazer or cardigan. As it gets colder you can put a button up white shirt underneath. Riding boots take this dress out of the 60's into present day fashion.