Pencil Skirt Designer Gray

The Label: Started in 1856 by Thomas Burberry, the brand went from outfitting WWI officers (thanks to the invention of gabardine, a water-resistant material they patented) to Holly Golightly in 1961's Breakfast at Tiffany's. Burberry's signature pieces are the trench coat and the plaid (actually "check" if you're a Londoner). The Look: Clean lines, classic style, and traditional colors (offshoots of the red, black, beige, and white Burberry check). The clothes are striking in their simple beauty. The Designer: Christopher Bailey went from the Royal College of Art to spending a year at Donna Karan's studio in New York. Six years into designing the women's collection under Tom Ford at Gucci, he was hired to resuscitate Burberry. Since his arrival at the label, Burberry has earned a record $167 million in profits.