For the winter and spring of 2023, I was starting to figure a few things out with my appearance. We purchased a few simple items to wear around the house to help me feel more comfortable. Cathy purchased some makeup for me so I could practice, and I got a fairly nice wig to help me complete my appearance. This was done in the security of the home. This would be mostly in the evenings after dinner and occasionally on the weekend. On one hand it wasn’t enough, and on the other it was too often. Maybe that’s for another post?
One thing I uncovered with my therapist is that over the next few months, I would need to start getting comfortable with my appearance out in public. If the plan was for me to transition full time within the year, I would have to be comfortable being myself anywhere. This was a time where only our closest friends and family knew about my transition. We were not going to risk this in our hometown.
It was April and we had booked our family vacation for the end of June. Summer was also coming, and I had no idea what I should wear for the warm weather. Fortunately, Cathy had gotten some help working on her wardrobe late in the previous year. Cathy had also pre-emptively confirmed that this personal stylist was an ally to the LGBTQ+ community so we thought we would go together and spend a day getting some outfits and ideas.
The Trip to Halifax
We drove a few hours to Halifax for the weekend not really sure how the whole weekend would unfold. The focus was all on Cathy at first while I sat in the changing room and just took it all in. I never realized there was so many differences between clothing styles and variations in sizes. What seemed to look very similar could look very different once you tried it on. I learned a lot in those couple of hours. At the same time, I was starting to get nervous about trying on clothes for me. I briefly thought about calling it all off but was too excited to stop now.
Now for My Turn
After paying for the outfits that Cathy purchased, we changed stores to one where our stylist had prepared some things for me to try on. Up until this point I had been in male mode which wasn’t going to work going forward. When I got into the changing room with a few of the outfits, I also put on my wig and bra that I had brought along. I don’t think it would have mattered what outfit I would have tried on first. Whatever I tried on, I knew I would love it. I remember peeking my head out the door and making sure there was no one around before coming out to show them. It wasn’t necessary as we were in the last stall and it wasn’t very busy, but I was so nervous. I tried on a bunch of other things from tops to dresses to jumpers. A lot of the sizing was wrong and didn’t quite work. When you’re tall for a woman and you don’t have much of a figure to hold things in the right places, it makes sense. A couple of times I was on my own coming out of the change room. Cathy was in the stall next to me and the stylist went off looking for other sizes or help from someone at the store. I started to get more comfortable though and feeling very good about how I looked. We bought a number of things from the first store and then headed to another. Step one was to change back to male mode for the walk through the mall… sigh. I wasn’t quite ready to be out there.
The second store wasn’t as successful but I did pick up my favourite jeans and top from there so it wasn’t all bad. While we were there, we had a look at some of the shoes too. Nothing fit though. They don’t typically carry my size in women’s shoes at most stores. That was a full day, starting just around lunch time and ending when the stores started closing.
When we got back to the hotel room, Cathy was nice enough to let me put on a fashion show for her. I was just so excited and must have been a bit annoying.
The Next Day
The following day was another day of so many firsts. I don’t remember much about getting ready in the morning or how I chose the outfit I wore. I do remember the decision that this was going to be the first day that I would get to be me, in public, for the first time. Stepping out of the elevator into the lobby of the hotel is an event that I have etched into my memory. I remember a lot about that breakfast and just the awareness of everything and everyone around me. Thankfully, we weren’t seated in the middle of the restaurant, we were tucked in a little nook against the windows. The picture that Cathy took during breakfast is one of my favourites of all time. Oh, and the French toast with fruit was amazing too. Cathy did most of the talking when the waitress came around but I can’t remember if she ordered my meal for me or not.
Next Stops
We then drove on to continue with the process. Cathy was having all of her outfits coordinated so that she could see which items went well together. It was a nice morning and I remember appreciating the opportunity to be there as Brooke. I learned a lot about what items pair well with others and catalogued a lot away in my mind.
On the way home we stopped in a couple of other shoe stores. We hoped that may have had my sizes in stock. Going into these places create a wide range of feelings. On one hand, it exhilarating to finally try on clothes and shoes and be yourself, but at the same time, I was constantly looking over my shoulder fearing that someone might say something stupid. What put me at ease was when one of the workers came over to Cathy and I while I was trying on some sandals and asked “Do you ladies need any help with anything?” Yet another first for the day; getting addressed as the gender I feel I am, by a complete stranger. We did manage to find a couple of pairs that I could wear but had to order another online. All in all, very successful.
This was a weekend that I don’t think I will ever forget. I’m so grateful to have a wife willing to help me through it all. Cathy put up with my insecurity and nerves. But, I know it put a lot of strain on her too. She stood guard and was ready to pounce if needed, all while I was experiencing a euphoric moment and getting to be who I really am.