Jay asks Ashley if she had considered wearing a wig until her hair had grown out to a length that she felt was more feminine. Ashley answers a question from a viewer about her views on men wearing women’s clothing as she was growing up, including performers like Eddie Izzard and comedy troupes like The Kids in the Hall and Saturday Night Live. Jay also checks in with Ashley whether her early explorations with women’s clothes had any erotic subtexts.
They also chat about shopping for clothes, from her interactions with salespeople to arbitrary clothing sizes and the chicken-and-egg problem she faced as she was kicking off her transition.
Ashley tells the story of her first trip to any ladies’ room (hint: it was at work, sort of) as well as the sense of belonging she felt when she first went to a crowded one.
Ashley offers a tip on retaining supple skin under the eyes and talks through an idea that might help reduce the chances of chipping her nails while fishing through her purse for her keys. Lastly, Ashley shares a short time-lapse video montage of self portraits she had taken over the past few months using the “Everyday” iPhone app.
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Ashley celebrates her first week presenting as her gender full-time, with warm words and open arms from her coworkers, a more comfortable wardrobe (as well as a new laptop bag), and some entirely unremarkable bathroom visits. She and Jay also talk about how it’s been different carrying around one’s day-to-day items in a purse rather than a wallet nestled in one’s back pockets (or, in Jay’s case, a messenger bag).
Ashley recounts some early shopping trips with friends soon after she had come out to them and how they had come along with her for a gleeful day of shopping while also playing the role as sort of a fashion tour guide to help Ashley learn the ropes of her new clothing options. She also reminisces about a recent trip to Nordstrom in which they not only had shoes in her size — oodles of them — but also shoe clerks with the attentiveness that made her feel like she had acquired her own shoe sommelier.
As time drew closer to her transition at work, Ashley sprang for a series of makeup lessons from both an independent makeup artist as well as one from her local MAC store. Eager to share some of what she learned, Ashley conveys how one can use a sponge wedge to help smooth one’s foundation and a trick that can make it easier to recover from small mistakes when applying one’s eye makeup.
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