We're starting with an oldie but a goodie — or baddie, depending on how you look at it. Before she was the Princess of Wales, Catherine was Kate Middleton, Prince William's girlfriend from St. Andrews University that everyone wanted to know more about. Though she was technically a commoner, Catherine came from a well-to-do family that owned a lucrative business. As such, she was able to attend prep school and, later, the prestigious university in Scotland where she just so happened to find her prince, literally. As she and William were connected publicly by 2004, Catherine started popping up on the aristocratic circuit, including this pictured 2007 visit. Attending day one of the Cheltenham Horse Racing Festival on March 13, 2007, Catherine truly embraced the fashion of the time and rocked head-to-toe brown — though it really was not flattering, in retrospect. 

Starting with the silhouette, the skirt length on Catherine's figure made her look shorter than she actually is (Catherine is quite tall, standing at 5'9”). Cutting her off at the mid-calf while bleeding into the boots she chose for the occasion, the look from the waist down did not flatter Catherine's natural, graceful look. Meanwhile, the jacket, though nicely fitted, also hit her at an odd spot just below the waistline, messing up the proportions even more. Along with the 2000s sunnies, this wasn't her best look.