Written by Jade R. Right near the top of my list of things I did not want to hear was the following: “Jade, you are best when you elevate. When you’re at your stride, when you are humming at your highest vibration, you are incredible. We haven’t seen that from you in a while.”

I’ve had many hard conversations over the past year after coming out as genderfluid, but this was one of the hardest, because it came from someone I’ve known since I was a child. It was from my agent, Gary Dakin who I’ve worked alongside for nearly two decades in an industry that can be called many things, but never easy. And it was after I spent a full month without booking a single job for the first time in my entire career, except for during the Covid shutdowns. Shit, I thought to myself. I’ve become a problem, haven’t I?

I met Gary when I was a 14-year-old model with only a year under my belt, fresh from signing on with Ford Models. I was the kind of teenager who didn’t follow trends or fashion, and couldn’t possibly care less what I was wearing or how I looked. I wore the same sneakers every day, rotated through three pairs of jeans, and wore whatever clean shirt was on the top of a laundry pile. Yet within my first few years of modeling, I was getting booked for countless shoots for Vogue, Cosmo Girl, and Seventeen Magazine, among others. I was a theater kid, after all, and captain of my high school’s improvisational theater team. That confidence and stage presence carried over onto set. People loved working with me, and I have enjoyed an extremely busy career since then, spanning 20 years. Even though I’ve always struggled to pick out clothes for myself, I have since learned how much fun self-expression can be through clothing, but it has taken years. I hit a roadblock when I came out as genderfluid and decided to go through with a social transition. 

I knew that transitioning in such a public industry and with such an established career would come with challenges, but I underestimated the hardships I’d face and wildly overestimated my capabilities to handle them on my own. Feeling comfortable asking for help continues to be a battle for me. Fighting back tears, my pride screaming at me not to ask, I took a breath and said, “Can you help me? I don’t know what to wear.”

After modeling for as long as I have, I thought I was done feeling insecure. But going through a gender transition as an adult feels like living through puberty all over again. The more I tried to find ways to express and present myself in ways that weren’t gendered female, the more I found insecurities I didn’t even know I had. Had my hips always looked like that? Has my chest? Is my walk too feminine? Is my voice really that high? I began viewing myself under a microscope, discovering countless new ways to doubt myself and even more things to feel self-conscious about. Because of this, I hadn’t dared to brave any in-store clothes shopping since I came out, over a year ago. How did I get here, with a successful career in fashion, yet afraid to go shopping?

“Oh my god, please, I love shopping, yes, I will go shopping with you, I will help you figure it out,” said Gary, sounding relieved that I finally admitted to needing some guidance. 

We set a time to meet, and that morning, I finally looked through my clothes. Everything on my rack screamed either “14-year-old boy with both anger and hygiene issues,” or “girl who just turned 21 and lives in cheap nightclubs.” Yep, I thought to myself, I need help. I grabbed a simple pair of men’s black jeans I had bought online and tailored, a fitted black women’s tank, also purchased online, and a worn-in men’s leather jacket I had found in a thrift shop. 

This look was easy, casual, and would allow me to disappear in a crowd. I’m someone who’s walked runways in New York and Milan, who’s been on the covers of magazines, who’s done morning show interviews and red-carpet events. I realized, looking at myself now, I want to be able to disappear? I hadn’t noticed the slow decline of my self-esteem until it sank this low.

I struggled with whether or not to put on a bra or a chest binder. My gender is very fluid. I never know until I wake up and start getting dressed, which is going to feel more like home. I was feeling masculine that day, so normally I’d wear a binder, but I wasn’t sure if I could. I’d been modeling exclusively women’s fashion for years. Shouldn’t I be trying on new work clothes with a bra? I stood with one in each hand for a few minutes, before deciding to wear the bra, and I put the binder in my bag. I figured that if looking at myself in the mirror today made me want to hurl, at least I’d have it with me and could just change. Despite being someone whose job it is to be comfortable in front of mirrors and cameras, I avoided the mirror on my way out the door.

After asking a sales associate, we learned that the very first shop we walked into didn’t carry my size in-store, only online. This isn’t a new experience for me. This particular insecurity, at least, I can handle with grace. We thanked them and walked out. I remembered a few stores that do carry my size, so we moved on to those. I couldn’t help but ruminate on the fact that this kind of shopping experience is made even more difficult for plus-size trans people just because of their size. Being forced to shop for clothes solely online while others can enjoy in-store shopping is a degrading and dehumanizing experience, regardless of gender.

Gary selected some clothes, and when I stepped out of the fitting room in the first outfit he picked for me—an amazing pair of plaid culottes and a turtleneck in the same color family, both from the men’s department—I felt okay. The clothes themselves were great, the style suited me very well, Gary had put together a phenomenal full look, and the fit was perfect. But when I looked at my chest, I shrank. That day, it just felt wrong.

He noticed something was off, and asked, “You don’t like it?” 

I said, “No, no, I actually love this outfit, a lot. It’s just—can I try it on with my binder instead?”

When I came back out wearing my chest binder I was standing taller, and I actually wanted to check myself out. I felt great about myself in a way I hadn’t felt in quite a while. But at the same time, I was hyper-aware that I had just shown my insecurities to someone I admire. I struggled with my words. 

“Thank you for helping me; this is just really hard,” I said, tears forming in my eyes.

“What part is hard? Jade, you can talk to me. It’s me,” said Gary.

“I know. All of this is hard for me. This feels like going through puberty again, but as an adult. I don’t know how to deal with feeling insecure. It’s agonizing. It’s awful,” at this point, the tears were streaming down my face. Fingers shaking, I wiped them away before they could fall onto my new sweater.

“I’ve been so lost trying to figure this out. There’s no guidebook for genderqueer fashion. There’s women’s and there’s men’s but there’s nowhere for people like me,” I replied. At this point, I felt like I was on the verge of a breakdown, praying that a sales associate wasn’t about to round the corner and face the bundle of awkwardness that was me at that moment. 

“I feel like I’m 15 again, and I hate it,” I laughed, remembering all the conversations I had with him when I was an actual 15-year-old learning how to navigate a professional career. “You’re dealing with teenage me again.”

“Listen,” he said, “we got you through it the first time, and we’ll get you through it this time, too.” 

We checked out with a gorgeous selection of items from both the men’s and women’s sections, then visited another store. This one was much more crowded, and after we filled a shopping bag with items from both sections, I hesitated, thinking about which dressing room to use. At the first store, there was hardly anyone else around; I hadn’t even thought about it. But here, I would see other shoppers in whichever room I chose, and worse yet, they would see me. Have I really fallen so far that I’m afraid of a dressing room?

Standing on the men’s floor, I froze, “Can I even use the fitting room down here?” I looked at my shopping bag with items from both floors, “Can I bring this up to women’s?”

“Whichever room you feel more comfortable in, we can use,” said Gary.

“I’d prefer men’s, but I think I’m safer in the women’s,” I said. “Women are usually nicer; I know I won’t get beat up at least.”

“You’re not going to get beat up, you’re going to be okay,” he said. I thought to myself, maybe because we’re in SoHo, he’s right. I stood still, incapable of making a decision.

“If we go to the men’s dressing room, I can probably go in with you at least,” said Gary. I wasn’t sure I’d feel comfortable in either, so we went to the men’s fitting room. “Are you comfortable here?” he asked me. I nodded.

 I found a nice jade button-up (I do love wearing my namesake shade of green), and a couple of jackets from both departments. Before we made our way to check out, I gave him a hug that I hope conveyed the immense feeling of gratitude I had toward him for taking the time to help an overgrown teenager regain some self-esteem. I did manage to hold in the rest of my tears until I got home and sat at my laptop to write this.

It made me want to say ‘thank you’ to anyone who’s taken the time to be gentle and compassionate to the trans people in the early days of their transition, to elevate them and help them find their confidence. We live in a world that reminds us all too often that we don’t belong here, that there’s no space for us. Adjusting to living in this world as a trans person and feeling good about yourself when that’s the experience you have is extremely difficult. 

The way my confidence absolutely shattered when I transitioned has shocked me to my core. But for me, I know the level of self-esteem I can work my way back to having. I’ve had it before, and I can get there again if I continue to ask for help from the people who love me. I can’t imagine what this feels like for people who don’t have the supermodel confidence I had to begin with, or for people who don’t have any friends or family members who support them. This world needs to be better for trans people like us—and it will get there. In the meantime, remember that you are worthy of being seen, you deserve to take up space, and never be afraid to ask for help. Transitioning is hard, no one should have to do it alone. —Jade R.