How Do I Look?Season 92008 · 10 episodesEpisodes1Taking Steps Toward SuccessThe nonprofit organization Dress for Success assists a former drug addict as she begins a new career.2The Rock-T, Bride-to-BeA 25-year-old woman enjoys wearing rock-band T-shirts and messy jeans.3De-PLUM Your WardrobeA Chicago woman exhibits a passion for purple.4Don't Be a Boob About StyleTwo friends and a Hollywood stylist assist a preschool teacher whose wardrobe choices are anything but wholesome.5How Not to Play Dress UpA mother is scolded for her childish clothing selections.6Making Over a Dreadful StyleA woman's homemade clothing and terrible hair are called into question.7Spicing Up a Wannabe WardrobeA former high-school "it" girl lets her appearance go in the years since graduation.8The WEIGHT Is OverA recently divorced mother loses over 100 pounds but cannot shed mementos from her past.9The Hoochie HunterA Texas woman who loves to hunt wears camouflage clothing during the day and provocative outfits at night.10The Not So Hip HippieA 43-year-old woman wants to meet a man but her dated hippie wardrobe is holding her back.Season 1Season 2Season 3Season 4Season 5Season 6Season 7Season 8Season 10Season 11