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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 too for reasons of feeling alienated.

At some point though the core memberships started to change over. More members would stick around after discovering themselves, I think it was because they respected what the spaces were for them when they still thought they were just crossdressers. This did lead to a very definite tone shift in the groups though. I still have many dialogues with new members who didn’t stick around in the group longer than a week who were saying they wanted to talk to other crossdressers but felt alienated in the space they found. Eventually I left too for reasons of feeling alienated. It’s truly a troubling thing to balance a support group for people on the cusp of discovering their gender identity and also maintain a space for people who are looking to explore fashion outside the rules of gender. I commend the moderators of these groups for trying to maintain that balance, for me it just stopped working though.

You asked me about my thoughts on my gender as well. Something actually happened today that I think helps explain my thoughts on that. Earlier today when we met at Balzac’s you opened the door and said to me in a playful manner, “After you madame.” For me I quite enjoyed that you said that without second thought. I personally don’t put much thought into how pronouns relate to me, I refer to myself as a guy most often, but that’s really just a spoken convenience because gender comes up so much in conversation. Personally, I feel I would identify far more with, “Neven is a cat person” than, “Neven is a guy” because one says something I actively do and show and the other just describes the circumstances of which I came to exist. I really enjoyed that you looked past that part of me. Every day I dress up I get to look past gender notions in fashion and choose to express myself in a way that I feel best evokes the beauty and opportunity of being the human that I am, nothing should be off limits. I really appreciate you did the same with your language, whether it was just because you thought “madame” flowed best, or because you called your car, “chariot“ earlier that day and madame is such a fitting follow-up word, maybe you were even just testing the waters on how we talk to each other. Whatever it was, you made the active decision to express the beauty of your vocabulary and thoughts in the way that you felt fit best and didn’t let gender get in the way of that expression.

As for the question about Kingston communities, funnily I can’t really say much to that end. You can look online at which is supposed to represent all interests of LGBTQ+ members in the city, but I’m not convinced that Kingston is an optimal place to grow a community and that is actually due to a very positive reason. These days Kingston as a city feels relatively accepting in my experiences. As a cross-dresser I was constantly told I would eventually feel threatened for either political or ideological reasons were I to go out and be me. Now I’m sure this has been decades of progress in the works, but I’ve never felt the target of any kind of hostility here and when I go out dressing I usually have a pretty good time. In fact, I’d say my quality of life here in Kingston has improved by getting outside as a dresser because I’ve gained many experience and friends that as a closeted cross-dresser I just never would have had the chance to. People like you make Kingston a great place to be for people like me and to that end when you look at you’ll see there isn’t actually a support group event listed, but just the beers for queers events that are prominently shared. I think people here are able to find support from the community and not rely upon niche groups.

Finally, you were wording back to why it was I said I dress, and I got the impression that maybe my answer, “I just dress because I want to” isn’t all that complete or satisfying. That it leads on to there being a further answer not quite explored yet. Having done reflection in the time since we last talked on that subject, I think I can try to pull out a few more thoughts from my head. You say a lot about how people should love what they wear. Once we had that indigo modern victorian look going, I was tempted to joke and say, “You're going to have to fight me out of this for the next look.” It’s something I’d never felt like saying about menswear. In that moment I just felt confident, comfortable and inspired that it was tickling a part of who I was today. I think it comes down to the language of the clothes and how it speaks to me and to what I want to say. As a comparison to the arts, Vincent Van Gogh was a great artist but he created art through oil painting and not clay sculpting. It’s not assumed that he couldn’t sculpt, but he understood the language of oil paints much better. In a similar way, I find I understand the language of womxn’s fashion better than I understand men’s fashion. So when it comes to loving what I wear, I love what I wear when it’s womxn’s fashion because it’s a creative process that creates a look that speaks about me in a language I am confident I understand.

When there was a question, “should I embrace dressing?” a subtle secondary question was, “should I learn to love men’s fashion?” And I think the mental rebuttal at the time was, “okay, I can learn to love men’s fashion, I can study it and force myself to get better at it. Or, I clearly already love womxn’s fashion. Why am I trying to love something else when I already know what I would enjoy and I am denying it a chance?” I've found more about myself through womxn's fashion and I love my wardrobe in a way I never really expected to before I started.


I didn’t respond to Neven’s email in writing, but I made sure to bring it up at our next meeting and we continued the dialogue. When I read that message and think about our in-person exchange, I feel incredibly lucky to be around someone who is willing to speak open and honestly about their experiences with cross-dressing and the industry. I think that one of the greatest skills you can possess is to listen and be teachable.

Looking back, I realize Neven was in the middle of their journey with gender identity and I was asking questions they hadn’t even asked themselves. In our first exchange, Neven identified themselves as a male cross-dresser because as they explained above, it’s more convenient for others when in reality, they’re gender neutral. This is why I refer to Neven as ‘they’ rather than ‘he’ or ‘she’.

I don’t feel inconvenienced by that. I feel proud that I am choosing to honor someone else’s preferences.

I can’t help but pose the question, isn’t this how we should all be communicating with one another? With genuine curiosity for the way someone chooses to live? No trace of judgment, but rather an open mind, a compassionate heart and the humility to know that you might get it wrong, you might be corrected in your language, you might be called out—but at the end of the day, you’ll have learned how to be more compassionate towards others and accepting of the way they live their life?

Teachable moments are everywhere around us, we just have to be willing to put down our egos, open our hearts and listen. In fact, before I published this post I had a thought about the word, 'cross-dresser' and if those who express themselves through dressing in clothing that's associated with the opposite sex even like to be called that term. So, I asked Neven and the following conversation transpired:

This led me to google the term, ‘cross-dresser’ followed by, ‘inclusive language’ where I learned about person-first constructions that put the person ahead of their characteristics.

For example, instead of “a blind man” or “a female engineer,” use “a man who is blind” or “a woman on our engineering team.”

In my situation, I would say, “Neven is someone who enjoys cross-dressing” rather than “Neven is a cross-dresser.”

People-first language keeps the individual as the most essential element, which is important because there’s more to each of us than our descriptors. Further, we only need to mention characteristics like gender, sexual orientation, religion, racial group or ability only when relevant to the discussion.

You can learn more about inclusive language principals here.

An Opportunity to Represent the Cross-Dressing Community

In the midst of planning the Rainbow Photoshoot and all this honest conversation, I was hired by local retailer Fancy That Group to curate and style a Fall Lookbook that showcased their new product on the variety of customers that shop their boutiques.

I was in charge of everything from model casting, location scouting, hiring the photographer, styling 20 looks and providing creative direction for each. When it came time to cast the models, it was really important to me that we showcased a variety of bodies, ages, styles, and genders. I was not about to curate a lookbook full of thin white womxn, because a) I’ve already made enough of those featuring myself and b) I know we’re all tired of seeing clothes modelled on them. There’s nothing wrong with thin white womxn, but there is something wrong with only using this type of representation in fashion. It’s critical we make room for all types of beauty so that those who aren’t white and thin can see themselves in the photos online and in the media. This was my opportunity to do just that.

Neven came to mind immediately, although I wasn’t sure if they’d be willing to participate because of the nature of the ask—styling and photographing them in an outfit at work, and then in a different outfit outside of work in their hobby environment. I knew Neven was comfortable walking around town in their high-femme looks, but work is different—it’s where expectations of who you are and what you wear come into play and I know Neven wasn’t exactly dressing this way at work just yet.

As it turns out, the timing was impeccable. Neven had recently started a new job at Empire Life and was working up the courage to dress femme at least 3 out of 5 work days. This project was just what they needed to parlay into this new level of their personal expression and Empire Life couldn’t have been more receptive and encouraging. I know that not all situations turn out like this for those who express themselves differently, so I’m incredibly grateful to the people we chose to surround ourselves with.

The photos below are by Love and Exposure Photography, clothing is from Fancy That Group and styling is by yours truly.

Wrapping it up With a Celebration of Pride

Now it’s time to get into the Rainbow Photoshoot I’ve been alluding to this whole time!

The idea for a rainbow-inspired photoshoot came from Neven, who saw a ‘rainbow challenge’ on Reddit three years ago. They explain their reasoning behind wanting to take this challenge in one of their Instagram posts I’ve linked below.

Neven hired me to be their creative partner in crime in order to bring this idea to life and I couldn't pass up the challenge. As a big music buff with a particular affinity for Jazz music, Neven wanted to incorporate instruments into their version of this photoshoot concept— adding another layer of style and composition for me to consider. My job was to style seven different looks, source accessories to bring these looks to life, coordinate instruments and poses for each one, and choose a background colour that would compliment the creative direction. WOAH, right? Talk about a dream come true! I was a combination of excited, nervous and intrigued. My self-doubt came out to play every step of the way, which made it difficult to enjoy the planning process, but as soon I met with Neven to propose the creative and styling concepts, confidence started to outshine self-doubt and we were able to create something beautiful together that we’re thrilled to share with you all.

I look forward to sharing more work with Neven in the future and I hope you enjoy these photos as much as we loved bringing the vision to life.

The Rainbow-Challenge Photoshoot

To view all the photos in each slideshow, click the arrow on the right photo to navigate. All photography is by Duska Dragosavac in her home studio—the perfect companion who really brought our creative idea to life. Thank you for these incredible photos Duska!

The Blue Dress

The Orange Dress

The Yellow Dress

The Purple Dress

The Indigo Dress

The Green Dress

The Red Dress

If you enjoyed reading this post, you can continue to follow Neven's 'lessons from dressing' journey on Instagram here.

Thanks for reading!


Why I’ve decided to use“womxn” instead of “woman” or “women,” and why you should too:

The term “womxn” is inclusive to trans womxn, womxn of colour, and basically reclaims the word “woMAN” for us to own and redefine. Strong, independent, diverse: ”womxn” is inclusive. Womxn is empowering. We respectfully acknowledge that not all womxn have periods, and not all people with periods identify as womxn. Using this spelling is a necessary step forward for ClosettCandyy to continue nurturing our community, and having conversations that I believe are important. To learn more, check out this Medium article: Intersectional Feminism 101: What is Womxn?


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