This is an article about my recent weekend trip, en femme. It was my first time dressing 24/7, and my first time out and about during the day. Without getting into too much backstory, I think it’s worth noting that this wasn’t actually my first time dressing in public. About twenty years ago, when I was still single, there was a year in my life when I ventured out quite a bit. It was exclusively at night and mostly to a trans-friendly club. While it was fun and meaningful, it was also something I’ve never felt compelled to repeat.
When I think about what I might like to do these days, it’s quite different than when I was younger. The idea of a loud, crowded nightclub sounds absolutely dreadful. Instead, a leisurely ladies’ afternoon of lunching and shopping sounds more my speed. My wife is supportive and up for the adventure someday but finding the right time in our busy lives is challenging. It’s one thing to daydream about it, but it’s quite another to be crossdressing in a real-world situation. Thankfully, an unexpected opportunity gave me the chance to find out.
My wife and I decided to alternate weekends away to give us each a little break from the daily grind. I knew right away that this would be a perfect chance for me to dress in public again. My plan was to take pictures at the hotel, it’s been awhile for me in full makeup, and hopefully venture out for coffee or takeout, maybe even for a glass of wine, if I’m feeling bold enough.
The destination was a little town called Ojai, two hours northwest of Los Angeles. It’s an agricultural town with working tangerine and olive farms, but it’s also a popular tourist destination with lots of good restaurants and boutiques. Fun Fact: Ojai was also the home of the fictional Jaime Sommers on the 70s TV show, “The Bionic Woman.” I was hoping to channel some of the Bionic Woman’s strength for the weekend.
At the top of my list of places to possibly visit was a winery called Topa Mountain. As I drove into town, I noticed a sign out front that said, “Walk-ins Welcome.” Right then and there I knew that I wanted to make that happen, but I only had a few hours before they closed.
I checked in, unpacked, and set about transforming my face. I wore a midi-length shirt-dress with an abstract floral pattern in pastel colors with ruching at the waist and cuffs. I’m 6’1” and didn’t want to be an inch taller, so I wore my black ballet flats. My wife generously let me borrow her leather Madewell handbag and wide-brimmed, woven hat. And with my mask, I felt sufficiently covered and headed out the door.
As I walked down the long, winding path to the winery, I repeated my mantra for the weekend, “Acceptance over passing.” I entered the winery and was enthusiastically greeted by a young female hostess. I sensed right away that I didn’t pass but she was really sweet and made me feel comfortable. As the hostess walked me to the outdoor patio, she turned and commented, “I absolutely love your dress!” What a nice thing to hear! I could feel some people taking a little longer-than-normal looks at me as I walked past. And while my nerves were a little shaky, I did my best to project confidence and comfort.
My server, another cheerful young woman, took my order and complimented me on my lipstick. Once I took my first sip of rosé and had a little bite from my cheese plate, I leaned back and soaked in the experience. The view was breathtaking, with rows of grapevines in the foreground and sprawling mountains beyond. I missed my wife and wished we could be experiencing this together. I noticed that a table had asked their server to take a picture of them and thought I’d do the same. My server was happy to help and really got into it, shooting a bunch of shots from different angles. At one point, a breeze blew my dress up á la Marilyn Monroe in The Seven Year Itch and she captured it perfectly. As I left, the staff all said goodbye and asked me to come back soon.
On my way back, I drove by another tapas and wine bar that I’ve been to that happen to be open. Set in a stunning, old Spanish house with indoor/outdoor seating, their style is impeccable, every detail is on point. Three young twenty-somethings, two girls and a guy, were running the outdoor bar. I ordered a glass of wine and a bite to eat and ended up in conversation with them. The entire time, not one of them gave even the slightest hint that there was anything unusual about the way I looked. I felt natural and comfortable.
I returned back to the hotel around 7pm and ate dinner. I downloaded my pictures from the day and turned on the TV. “Family Guy” was on. It’s not a show I usually watch, but right away I noticed that the entire episode was in homage to “Tootsie.” What kismet! I had to watch it!
The next morning, I woke excited and invigorated from the previous day’s successes. I showered and put on my makeup. My outfit for the day was the one I was most excited to wear and seemed to be a good fit for Ojai – a sheer, long-sleeved maxi dress with a blue and white, tiger-stripe-like print. It’s very flowy and feminine, like a kaftan. I’d borrowed an orange beaded necklace from my wife. This time I wore my gold strappy sandals and the same hat and handbag as the day before. I really liked using my wife’s handbag as it connected me to her. It’s perfectly broken in and has the look of a real woman’s daily bag. I love those kinds of little details.
I snapped a few quick pics and headed out the door for my first, all-day, femme outing.
My first stop was to get coffee at my favorite local cafe. It was a surprise to see more people than usual standing around waiting for their orders. When it was my turn, I was again greeted with a big smile from a nice guy working the register. The morning was off to a good start!
There were many people that I guessed read me right away but remained content in pursuing their own business out of respect, or at least, indifference. The two longer stares I received were both from middle aged, suburban-looking women. One thing for certain; I was hyper-aware of everything around me and in a way I normally wouldn’t, which was an interesting way to move through the world.
To be continued…