I love seeing clients return over the years and watching their journeys evolve. Lauren first came to see me in 2019 when she was going by the name Katherine. Since then, she’s tried on a few different names before settling on Lauren, which she’s embraced for the past couple of years. That’s part of the magic and fun of being a crossdresser: you can reinvent yourself with clothes, hair, and makeup and even your name.
Over the years, Lauren has gone out shopping and dining with me in girl mode, taken a makeup lesson, and even done her own makeup and gone out on her own. After taking several months off from crossdressing in public, she decided to rebuild her confidence with a makeup lesson refresher and an accompanied crossdresser outing.
A Makeup Lesson Refresher
For this visit, Lauren came well-prepared with her own wardrobe, wig, shapewear, and sandals. She also brought fun finishing touches—her toenails painted white and pearlescent, white, press-on fingernails to match. She wanted a makeup lesson refresher but not a hands-on approach this time. Instead, we recorded video on her cell phone while I did her makeup, giving her a personalized tutorial she could replay at home.
She decided to wear a cute, cranberry-colored romper with sandals. I immediately suggested MAC’s Cranberry eyeshadow to match the romper’s color. We debated between brightening it with MAC’s Yes to Sequins or smoking it out with MAC’s Carbon. Lauren chose the brighter route to echo her summery vibe. We paired it with the soft pink, Gentle blush and Twig lipstick, a versatile pink nude. The final look felt fresh, feminine, and perfectly seasonal.
Studio Photoshoot
Once her makeover was complete, we headed into the studio for a short photoshoot. Lauren slipped easily into posing. These studio photos gave her a chance to capture her transformation and the details of her new makeup look before we ventured outdoors.
A Crossdresser Outing in Takoma Park
Our crossdresser outing to downtown Takoma Park capped off our time together and was the true highlight. Our first stop was the Progress Pride rainbow crosswalk, where we snapped whimsical photos with the iconic Roscoe the Rooster statue and the Takoma Park clock tower. Lauren humored me by listening to the legend of Roscoe, a free-range neighborhood rooster in the 1990s who became a beloved local character. His legacy lives on with a commemorative statue that locals decorate with a hat and scarf in the winter.
After photos with Roscoe, we walked two blocks across the Washington, DC line to Busboys and Poets in Takoma, DC. We ordered salads and girlie pink drinks—Lauren went for the “Grown and Sexy” cocktail while I enjoyed the “Self Care is the Best Care” mocktail.
Over dinner, we caught up on life and reflected on the experience of going out in girl mode. Lauren shared, “It feels really tense right at first, and then I adjust, like jumping into a cold pool.” That moment of transformation—the shift from nerves to joy—is something so many crossdressers and transgender women know well, and I love helping them make that leap.
Plan Your Own Crossdresser Outing
This experience upped Lauren’s confidence for doing her own makeup and going out in girl mode again. That’s the power of a crossdresser outing: it lets you live your femme identity beyond the mirror and embrace it in real-life spaces.
Are you ready for your own day of transformation? At Makeovers with Elizabeth Taylor, I offer crossdresser makeovers, photoshoots, and accompanied outings to help you step fully into your feminine self. Whether it’s your first time out or a chance to refresh your look, I’d love to help bring your vision to life. Read more about how to get started here.
Book your makeover and crossdresser outing today and let’s create memories you’ll treasure while increasing your confidence.
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