#1. The Dress

To pull of Anne's look, the first and most important item of business is definitely the dress. It's got to be modest, and while it should be slightly fitted, it can't be tight. Think of it as being "tailored" instead of "form-fitting." Some small details will add interest, but a solid color is best. A bright color, like red, will show confidence, but a similar shape in black, gray, or brown would be lovely and more appropriate in some circumstances. We love that there's some detail at the waist to show off her figure -- you can play around with belts if your dress is plain.