How Do I Look?Season 102009 · 20 episodesEpisodes1Unique Chic, or Freak of the Week?Twenty-three-year-old Crystal's extreme style scares people away, and she must tone it down to move forward with both her social and professional life.2An End to MenswearConvinced she'll always be ugly, Edith goes out of her way to dress in oversized clothing and must learn that she is capable of feeling and looking beautiful.3Grin and STOP Baring ItYoung mother Chastity wants to be taken seriously, but has a problem with dressing too suggestively. Jeanie shows her a more elegant style.4Ivy League RaunchTattooed Roller Derby girl, Ivy, has an abrasive punk rock look and an attitude to match, and must learn that you can be sexy and edgy without looking trashy or scary.5The Girl in the Red GlassesFormer child model, Kristy, no longer feels beautiful and must overcome family issues, update her style, and learn to flatter both her body and her personality.6Melissa TalwarA woman who frequently wears oversize sweatshirts and jeans needs to learn to dress appropriately for her position as the owner of a music company.7Carnivore CoutureAttention-seeking Lynn uses big fashion, hair, and makeup to feel sexy and must learn that trashy isn't sexy, bigger isn't better and let her beauty shine through.8Thirty, Going on ThirteenJeannie steps in to help Liliana, a 36-year-old mother who dresses like a teenager, and has moved back into her parents' home.9Matronly MarleighThirty-three-year-old wallflower, Marleigh, hates change, always plays it safe and dresses to blend in. Jeannie helps her come out of her shell and find her true identity.10The Unhappy HippyHeather has a wardrobe that is either handmade or from a thrift store. She must learn that she can be environmentally conscious and fashion-forward.11Perplexingly PurpleAlisa George is a 39 year-old mother who works for the state of California as a cashier at Caltrans and has taken her favourite colour to the extreme and become "The Purple Lady." It's time for Alisa to bust out of her purple shell and show us who's hiding underneath.12Mission KimpossibleAfter 7 years of stripping and a third child on the way, Boston native, Kim, has finally hung up her heels and stopped dancing. Now she must learn to class up and see that her trashy clothes prevent her from getting work and keep her children from respecting her.13One Sloppy MotherNicole is a responsible, single mother of a two year-old boy who doesn't believe she can ever look stylish with her hectic schedule, and must be dragged out of her sloppy, lazy, shapeless wardrobe.14Kindergarten CoutureTwenty-four-year-old Jen Marie is still wearing a twelve-year-old's wardrobe, and needs a more mature look to be taken seriously in her career and her relationship.15The Confused FashionistaWhen it comes to her own style, Rebecca can't seem to put two and two together, looking more like a fashion disaster than the fashion professional she is, and must simplify her look to stop hurting her husband and her job.16The Over-Coordinated DisasterVictoria, a 33-year-old mother of two, loves matched outfits a little too much and also pairs them with bad accessory choices. She needs to start dressing better for her family and career, but refuses to spend the time needed to coordinate separate pieces.17Earth-Friendly, Fashion-HostileLaid-back nature lover Forest is all about saving the earth and reusing as much as possible, never throwing clothes away. It's an attitude and style that keep her from moving forward even one inch in life, and keep everyone she knows at bay.18Covered and DiscoveredAfter being dumped by the father of her son, 26-year-old Tavara reacted by flaunting her body with everything hanging out all over, but she needs to learn that showing too much skin isn't appropriate.19A Charity Case for FashionKristen gives to charities and crusades for social justice, but her overall sense of fashion has taken the back seat in her life. She's careless when it comes to her style, and needs to see her own appearance as a cause worthy of compassion, too.20A New Style for a New LifeStephanie, a mother of four who suffered domestic violence in her past, doesn't have the worst sense of fashion but her limited resources are keeping her from looking her best. She needs a fresh start in life, and with a guest appearance by actress Halle Berry, she's about to get one.Season 1Season 2Season 3Season 4Season 5Season 6Season 7Season 8Season 9Season 11