Will is a 25-year-old from Alabama who needs to drop his hillbilly fashion tendencies for a sharper, more professional look, especially to be able to cut it in his new job. At 6' 3"" and 180 pounds, Will is tall and lean; however, his clothes are certainly not. Stacy and Clinton have to convince Will that his extra-large polo shirts and oversized pants are not the way for the new guy at the office to look.

Will also has a sock problem: all his socks are white and athletic — and he's wearing them with dark leather shoes! Last, to make sure that Will can make a great first impression, the WNTW team introduces him to an etiquette instructor who teaches him the subtleties of the proper business handshake, the confident walk and the memorable introduction.