Get Anna Wintour's Look: Anna's look is classic and expensive (she wears the best designers like Chanel). She favors simple lines and tailoring over softness or layering. Most of Anna's looks involve a skirt/dress around knee-length (which is perfect for her petite frame). Anna Wintour also loves prints and frequently wears print dresses. Her most iconic looks are fur (loads of it), huge black sunglasses and a perfectly shiny bob with bangs.