Celebrating Pride: My Experience With Cross-Dressing and Gender Identity


photos by Duska Dragosavac, styling by ClosettCandyy
 

I want to kick-off this post by wishing my clients & everyone in the LGBTQ+ community a Happy Pride Month as it comes to an end!! I haven’t always been as vocal as I could be during these celebrations, but it's never too late to start and I’m committed to being LOUD & PROUD in my support. I've been reflecting on how I can do better personally and what I can do to start having these conversations online. I recognize the importance of not only showing and speaking up, but also using my platform to share other people's stories.

So that's exactly what we're going to do today!

Over the last couple weeks I’ve been working to compile the magnificent story of my working relationship and friendship with Neven of @lessonsfromdressing. To be completely honest, I’ve been meaning to write three separate posts about our three magical projects for over a year—but at the end of the day, writing blogs often gets moved to the bottom of my to-do list. NOT ANYMORE BITCHES.

When I was pleasantly reminded it’s PRIDE MONTH while scrolling through Instagram one day (note to self: get an editorial calendar), I thought… NOW IS THE TIME.

And so here we are, celebrating Pride Month with a glimpse into mine and Neven’s experience with cross-dressing and gender identity in Kingston. It's been a bit of an undertaking to turn three projects and a 2+ year relationship into one cohesive story, but I've enjoyed the trips down memory lane and conversing with Neven to bring this post to life.

I want to use this post not only to highlight the projects we've worked on together, but to also have a conversation about cross-dressing, the importance of using language appropriately, expressing yourself through whatever clothing you want regardless of gender, and the responsibility I have as a stylist to represent a variety of beauty ideals on my website and across my social media platforms.

LGBTQ Pride Month is currently celebrated each year in the month of June to honor the 1969 Stonewall Uprising in Manhattan. The Stonewall Uprising was a tipping point for the Gay Liberation Movement in the US and the purpose of the commemorative month is to recognize the impact that lesbian, gay, bisexual and transgender individuals have had on history locally, nationally, and internationally.

And so here we are, celebrating Pride Month with a glimpse into mine and Neven’s experience with cross-dressing and gender identity in Kingston. It's been a bit of an undertaking to turn three projects and a 2+ year relationship into one cohesive story, but I've enjoyed the trips down memory lane and conversing with Neven to bring this post to life.

I want to use this post not only to highlight the projects we've worked on together, but to also have a conversation about cross-dressing, the importance of using language appropriately, expressing yourself through whatever clothing you want regardless of gender, and the responsibility I have as a stylist to represent a variety of beauty ideals on my website and across my social media platforms.


My Introduction to Cross-Dressing in Kingston

I first heard from Neven in January of 2018 when I received an inquiry via my website. Right away, Neven mentioned they’re a male cross-dresser that’s been building their wardrobe since February 2017 and has a tendency to buy single outfits rather than pieces that can mix and match. This is a very common challenge amongst the clients I work with, so although I didn't have experience working with cross-dressing specifically—I knew I'd be able to help.

I felt called to work with Neven for a variety of reasons. One, I don’t like to make anyone feel left out or excluded, so I didn’t want my lack of experience to potentially be taken as an excuse. Two, I felt as though I had the opportunity to normalize and destigmatize the art of cross-dressing through my platform. And three, I saw a major gap in my knowledge as a human and knew I could grow from this experience.

But did I also worry what others would think and if it would negatively impact my business? Yeah, I did, because I was letting the fear of stepping out of my comfort zone get in the way of my purpose.

You see, the ClosettCandyy mission is to empower EVERYONE to dress for themselves. And if I didn’t embrace this client? I would be dishonoring my own values. The reality is, I don’t want to work with anyone who would use this as a reason not to work with me.

Neven even felt compelled to ask me after a few months of working together if sharing our work on my social media has garnered any negative feedback. I’ve learned that most people who cross-dress are very secretive and not everyone in Kingston who expresses themselves in this way know about one another. Thankfully it hasn’t brought any negativity my way, and if anything, it’s allowed other people who express themselves in the same way feel comfortable enough to reach out to work with me.


Leaning into Discomfort for Growth and Understanding

Our first few meetings were in the Spring of 2018 to discuss wardrobe goals. The energy was a bit awkward between us, but I knew that feeling would eventually subside the more time we spent together and the more comfortable I became with asking questions. I knew nothing about cross-dressing going into our relationship, so I made a point to clear the air and be upfront about how I was feeling. I expressed that I had questions rooted in curiosity not jugement, that I wasn’t sure if I was going to ask them appropriately, and to let me know any time my language was incorrect or inappropriate.

I not only wanted to understand how to best use my skills, but also to ensure Neven felt comfortable being their authentic self around me. At the time, I had a few more personal questions than Neven was ready to answer, so I respected that and made peace with not knowing the answer to everything. These particular questions weren’t going to help me do my job better, they were more to understand Neven as a person. But if someone isn’t ready to answer, or even knows the answers to the questions you're asking—it’s your responsibility to accept their boundaries and not push back just because you feel a certain way. I had the knowledge I needed to help Neven with their wardrobe and I felt confident in the work we were doing.


When we first met up in 2018 to style outfits using the clothes they already owned, I asked if it would be best to photograph flatlays of the outfits or if they wanted to try on the outfits for me so I could work with proportions in real time. Because it's quite an undertaking for Neven to get into femme-mode (adding certain pieces under their clothes to create the illusion of hips, breasts, etc.), we felt it was the best use of my time to go the flatlay route. Neven would later try the outfits on and take a self-portrait to capture the look. It's important for me to see what the combination looks like on the body so I can get a better understanding of how Neven's clothes fit. I've included a few of my favourites below.

Fast forward a year later to one of our styling sessions for the Rainbow Photoshoot, I was much more comfortable asking Neven questions that came to mind and I realize now this wasn’t exactly the proper environment to do so—our minds were focused on an aesthetic and my questions were quite deep. I was really into watching the show Transparent and I would ask Neven questions through the door while they were changing their look. But once they came out of the room, the conversation would shift to the dress and style at hand. It wasn’t until Neven followed up with an email a few days later that really helped me understand there is no black and white answer to the questions I was asking, and I can’t thank Neven enough for the insights I gained from this thoughtful response.


Hey Jesse,

You asked a couple interesting questions today and I meant to give them a proper answer but the topic never really came back around before you left. I didn't want to ignore them because they were very fair questions for a friend to ask, and I don't want to let them linger as those, “they didn’t answer last time, maybe I shouldn’t ask again” type of questions. Hopefully this gets somewhere closer to understanding and gives some insight to my...I don't know what to call it, philosophy or self-analysis? Maybe just keep it simple and call them as they are, experiences? Anywho, I’ll do my best, and again thanks for just going for it on the question and not being afraid that I might not want to hear these questions. I appreciate that.

You brought up a show, Transparent, as the first bit to one of your questions. You brought up the conflict in part of the series where a transgender individual is meeting with a group of cross-dressers and feeling out of place. I somewhat jokingly said back at the time with “too real.” To expand on that, I partially said this because I’ve spent a lot of time on both sides of that coin.

When I started experimenting with cross-dressing, I wanted to make an effort to be social about it. I’d gone it alone and failed so many times I wanted to get to know other people who had the same struggles. I came across a few online chat groups dedicated to cross-dressing and found a lot of growth in these groups. When I first joined, they were primarily formed of cross-dressers and the daily chats felt like a productive place for me to be. From my perspective, something that wasn’t that uncommon was the use of cross-dressing as an exploratory step towards understanding one’s own relationship with gender. Over time, you’d see early members realizing they much preferred the gender they were exploring over the one they were assigned and leave upon this realization. I think they realized there were questions they had that the group just couldn’t answer. Honestly, I miss some of these people, but I’m glad they moved to find more about themselves. Eventually I left