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When I couldn’t tell the world I wanted to transition, I went to Dressbarn

The store played a pivotal role in two key moments of my life.

Justin Sullivan/Getty Images

I thumbed through racks of designer dresses at my local Dressbarn. Years earlier, my wife had told me that the store was for “frumpy old ladies.” But now, after so many big, sudden changes in my life, I could only laugh that I was back in a Dressbarn again, alone.

I was on a mission to find a very important dress, something suitable for one of those special memories that you know will stay with you for the rest of your life.

Suddenly, I saw it: the little black Calvin Klein dress with stripes.

“No fucking way,” I muttered to myself, walking quickly toward the clearance rack where it hung.

It was just as beautiful as I’d remembered it to be. I glanced at the size on the label and nearly shouted when I saw it would fit me. I took it off the rack immediately, before anyone else could get to it (though I’m pretty sure I was the only customer in the store at the time), and headed to the fitting rooms.

It fit like a dream. I knew this would be the dress I wore on the first day of the rest of my life as a woman. It was meant to be.

Though I didn’t always have the right language for it, I’ve had gender dysphoria since I was a child. Once I reached adulthood, it took all my effort to repress my gender-related feelings and try to live the life expected of me. I married the first woman who fell for me and we went from there, building an amazing life together. For more than a decade, I managed to keep my dysphoria at bay, relegating thoughts of my gender identity to moments of solitude.

But by 2015, it was becoming more difficult to contain, and fleeting feelings about my identity had long since started taking up more and more of my brain.

Actually expressing my true gender, however, was a much more difficult proposition in a house I shared with my spouse and young child. Eventually, I began acquiring a small, secret wardrobe of women’s clothes, which I kept in their original bags in an attic crawl space that I was pretty sure my wife had forgotten about. I was hoping beyond hope that this little bit of escapism could soothe my dysphoria enough to keep living the life I was supposed to.

As I was coming to terms with my identity, I kept noticing a particular black dress with wide white stripes on the skirt. It looked good on tall women, and, being 6-foot-2, I definitely took notice. I would see iterations of the dress everywhere, worn by models on red carpets and by customers at the bank where I worked.

However, I wasn’t ready for nicer dresses then, preferring to keep it simple with cheaper pieces from places like Target. If I had known then what would come of that secret stash of skirts and tops in the crawl space, I might have abandoned the idea immediately.

The local Dressbarn was tucked away in a shopping plaza in a town not too far from our seaside Maine abode. My wife never shopped there, frequently citing the aforementioned “frumpiness.” The first time I’d entered that Dressbarn on my own, though, was to find a dress for her.

We weren’t the type of couple who typically did elaborate dinner dates, preferring instead to have meals with the kiddo or a night out at the movies. Our marriage had grown into the comfort of familiarity. I wasn’t the greatest spouse, honestly, and my dysphoria had caused me to withdraw a little from the relationship.

My crawl space excursions had reinvigorated me lately, though, and I wanted to kick-start our relationship. Besides, we had recently decided to try for a second child.

I had made reservations for Valentine’s Day weeks earlier and arranged for my wife’s parents to watch our daughter for the night, but it quickly dawned on me that my wife didn’t really have an outfit appropriate for such a fancy dinner out. I decided at the last minute to buy her a new dress for the occasion. Dressbarn just happened to be the closest women’s clothing store to my work. It would have to do in a pinch.

As I entered the store, I immediately felt out of place. I was at that awkward place in my self-exploration process where I was still fully acknowledged by society as a man and wasn’t confident in my own claims to femininity; that was confined to my private moments. In the Dressbarn, with its racks and racks of dresses and women’s clothes, I was still a fish out of water.

A sales associate approached me. Even though I knew what I was looking for, I took her up on her offer of help, hoping that playing the bumbling husband role wouldn’t arouse any suspicion. I told her I was looking for a dress suitable for a high-class restaurant, and she led me over to their designer section.

“What size is your wife?” she asked. I responded without hesitation. “I’m impressed,” she said. “I don’t think most guys have any clue what dress size their wives wear.”

I laughed nervously and turned my attention to the dresses surrounding me. It was almost too much for my senses, being surrounded by these garments I so desperately wanted to wear myself. And then I saw it. The dress with the white stripes. It was then I learned the simple little black dress I had been pining for was made by Calvin Klein.

I swallowed my excitement and started thumbing through the available sizes; they didn’t have one that would fit my wife. I glanced over at the associate, who was briefly distracted by another customer, and started looking at the larger sizes as well.

Alas, they didn’t have one in my size either. Besides, I asked myself, how would I explain buying a dress five sizes larger than what I just told the associate my wife wore? I quickly dismissed those thoughts. Eventually I chose a gorgeous emerald green dress for my wife that I thought would make her hazel eyes and reddish-brown hair really pop and went home to get ready for the date.

The night was magical. We ate more amazing food than each of us could imagine. Our conversation was light and flirty; it reminded me of when we were first dating. Thoughts of that Calvin Klein dress couldn’t be further from my mind as we reconnected emotionally and romantically. At least temporarily, the role of doting husband suited me.

The thing about secrets is they tend to reveal themselves in the most inopportune moments.

The two weeks after our Valentine’s date were the best my wife and I had had in a long time. We were close, affectionate with each other. I was more engaged with the family. I hoped I had finally reached a state of relative calm. Unfortunately, my dysphoria had other ideas.

I would occasionally take sick days from work to just dress as and be myself. One day in late February, I took one of these “dysphoria days.”

I helped my family get off to work and day care, and then got dressed. My number one rule for my girl stuff was that I refused to use or wear anything of my wife’s — none of her clothes, none of her makeup, none of her jewelry. It seemed disrespectful to avail myself of her things without her permission.

That day in midwinter was spent just lounging around the house in a white women’s tee and a striped skirt, but I added eye shadow for the first time. Honestly, I looked like a frightened raccoon, but I didn’t care. The only problem was … I didn’t know how to take off my makeup. It’s laughable, thinking back on it now, but I spent the better part of an hour scrubbing my face and eyes and could still see remnants of the eye shadow.

I had ordered a pizza to pick up just before my wife came home with our daughter. As soon as she saw me, she asked what was wrong with my eyes.

“It looks like you have two black eyes!” she told me. I panicked and rushed to the bathroom, my brain racing. I again scrubbed my eyes with soap and water, but it didn’t make a difference.

I rushed out of the house, not making eye contact with either of my family members, and went to go pick up the pizza. About five minutes later, my wife called.

She had found the crawl space.

When I got home later, we shut ourselves off in the den to talk, not eating a bite of the pizza. What came after was perhaps the most uncomfortable conversation of my life. I had told no one about my gender feelings and always managed to hide my cross-dressing sessions, which had gone on since my childhood.

My wife looked at me with cold, hard eyes. It scared me.

“Are you a Bruce Jenner?” she asked. At the time, Caitlyn Jenner hadn’t come out to the world yet, but the tabloid press was openly speculating that she was beginning a gender transition.

“No.” (Yes).

“Do you want to be a woman?!”

“No.” (Yes).

I begged and cajoled her to give me another chance. That I wouldn’t do it again. Reluctantly she agreed, with a few conditions. She made me throw away my secret stash of clothes and makeup and promise never to wear women’s clothes again.

What choice did I have? She and my daughter and our beautiful home together were all I had. I agreed and got rid of the clothes that night.

For a while, I did my level best to conform to the role of husband and father. I even tried to grow a beard, hoping I could “man up.” I slept on the couch and my wife and I didn’t speak a word to each other for the next week. And when she did, those words carried so much weight.

“I have some news to share with you,” she said to me as we both stood in the kitchen. “I’m pregnant.”

The embrace we shared in that moment is one that still brings tears to my eyes. We kissed and gazed at each other. “Great fucking timing, huh?” she quipped as we both laughed nervously.

My second daughter was born that November. But by March of the following year, my dysphoria became too much to bear. My wife did her best to come to terms with my coming out, but we broke up when I told her I was starting estrogen, and I moved out shortly afterward. Great fucking timing, indeed.

October 3, 2016. I had the date picked out months in advance. That would be the day I officially transitioned at the bank where I worked. Because I was the first employee ever to transition at my company, human resources worked extremely hard to accommodate me. I was to transfer to a new branch where the customers didn’t know me, and get a fresh start as Katelyn.

I was living on my own for the first time in my life, making excursions in public as a woman, nervously using the women’s bathroom. It was a lot, but it never felt like too much to handle because a large part of me knew this was what my life should have been from the beginning.

My body was changing quickly because of hormone replacement therapy, and I was new to wearing women’s clothes outside around other people. It took a long time for me to figure out how to dress the awkward body I was quickly developing; I made a couple of trips to Macy’s for some professional staples and trips to Target for casual stuff. Blowing my entire clothes budget on fall wear left me with nothing for the other seasons, but there’s no manual for transitioning and I hadn’t thought that far ahead yet.

Everything was falling into place except for one thing: an outfit for my first day at work as my true self. Here I was, a 34-year-old trans woman going through a second puberty. I had no idea how it was going to go. My new coworkers seemed excited to have me, but it was impossible to know how customers would react.

Would they clock me as a trans woman and react negatively? Would they be too busy going about their lives to even notice? The branch was in the liberal oasis of Portland, Maine, but even socially liberal people can be transphobic. Once again, I was pressed for time and wanted something extra special.

I knew Dressbarn would deliver, just as it had for that special night with my now-ex-wife. I walked in this time as Katelyn. This time, I knew I belonged.

My first day at work in that black Calvin Klein dress was perfect. (Aside from, ironically, my first customer of the day demanding to speak with a man after he refused to accept my explanation for a bank policy. Welcome to womanhood, I guess.)

Now, nearly three years later, I look back on that lead-up to transitioning at work with some bemusement. What a scared little butterfly I was, emerging from my cocoon.

Earlier this week, Dressbarn’s parent company announced that it would be closing all 650 locations to focus on more profitable brands, and I’m sad to see my sentimental favorite go. I have bought many dresses since then, but I have a special place in my heart for that particular Dressbarn, in a parking lot between an Olive Garden and a Super Cuts. I look at the store now like I look at my manhood — it was there when I needed it most, but in the end, it couldn’t last. I’m going to miss the place.

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