Explorations of gender and curiosity through clothing.

What putting a man in lingerie for the first time taught me about myself.

Grace Van Der Velden
6 min readOct 21, 2021

I recently put a man in lingerie for the first time. It was a cream lace bodysuit covered in frills at the shoulders, and a plunging V-neck that revealed his hairy chest perfectly. It was the most feminine piece of clothing I owned, but it only made me feel the way I thought it would when I saw it on him.

Through personal exploration, in private, with a partner, I have found freedom, joy and ecstasy that I did not know was possible.

When I saw my partner wearing my lingerie… something inside of me budged, knocked loose, and a new feeling started pouring out. It released a flood of curiosity and power that I had never experienced before, but had been trickling in and pooling inside of my mind for a long time.

In the past, I have felt disallowed to explore expressions of gender and emotions through my style choices. What I put on my body had always felt like a performance meant for everyone except myself. My clothing was another way to people-please, and put myself on the backburner.

But now, I want my clothing to be a physical indicator of everything that flows through me — my thoughts, emotions, masculinity, femininity, and curiosity.

I am learning to follow those feelings — to shine a light into every nook and cranny of my own imagination and creativity, rather than let them be covered in the cobwebs of societal expectations. I am learning to sit with a question, and see what answers I find within myself first, rather than seeking external validation. I want to pursue niche experiences, an emotional reaction, a moment of body euphoria that I had never considered before — ones that are all caught up in the context of clothing and what it means to be the person inside of them.

For the first time ever, I am allowing clothing to become a deeply personal journey.

I consider myself a passionately casual thrifter (yes, oxymoron…. but I don’t plan that shit out! Amazing thrifts always fall like manna from heaven — when you need it most but least expect it). On top of my growing second-hand wardrobe, I am a long-time knitter and amateur garment maker. These are the tools I use to explore a personal style that has no bounds. Depending on my mood, I knit with different colours or fibres, and can immediately see how it feels on my body. More importantly, I can monitor the exact emotional response to how that fabric, shape, colour, or texture feels. I can ask myself what it says about me, and what it tells the world about me.

Up until recently, I had not thought of my style choices as some kind of personal message board. But I want my clothing to tell a story.

I want to wear clothes that provoke questions, that encourage curiosity, and that embrace both physical and emotional comfort. In the same way that I wouldn’t squeeze myself into jeans that don’t fit my wonderful body, I can no longer force myself into a flowy blouse or a slinky dress that does not reflect how I see myself — as someone who embodies masculinity and femininity in completely unique ways.

There are so many aspects of traditionally ‘feminine’ clothing that I simply cannot relate to, and if I do, I’ve usually added something that edges it out and chunks it up. When I was a kid, I used to play dress-up for hours. I would wear all sorts of family hand-me-downs from the 50’s, 60’s, 70’s, and 80’s. These pieces were all living stories to me, and allowed me to explore boundless characters and histories.

In this childhood world of play and whimsy, I was ungendered.

I was playing a character, and yet I was also authentically myself. I could be a newsboy with a cap, yelling ‘EXTRA EXTRA’ at my toddler sister, while also wearing heels and a pearl necklace to serve tea to my dolls.

Rules didn’t apply. I wore what felt right. What those clothes meant to me flowed freely from my uncorrupted mind. I didn’t need to think through how I would be perceived by others, and the feelings within my existed without labels or expectations.

But somewhere along the way, I was told that was wrong. I was told to be uncomfortable in my own body, and to question everything that I thought felt right. I was told to consider others before I considered myself. I was told to present myself in a way that was palatable or digestible for others.

As a teen, I felt uncomfortable wearing anything other than jeans and a plain t-shirt. I was an athlete who refused to wear sweatpants and baggy jerseys, for fear of appearing ‘too masculine’ when I already spent most of my time playing rugby or slamming girls into the wrestling mat. And yet, I was also so uncomfortable in my femininity that refused to wear dresses or a colourful blouse unless it was Sunday church or a family wedding.

I have come a long way since I was that insecure 16 year old. Thank god. But I know that remnants of that discomfort, of those expectations and fears, still cling to me like cheap polyester.

I am forced to ask myself what is feminine, and what is masculine to me?

I do not believe the answers to these questions are universal. My personal understanding of each is informed by my own experiences and the models I have in my life.

For example, I have always felt like playing rugby was a deeply feminine experience. A sense of support through physical exertion, and the emotions that come out during the game, have always helped me connect to my body and its own femininity. If anything, being covered in bruises after a game would encourage me more to wear a dress. It was through that contrast that I felt completely held and represented by my clothing.

On the other hand, I see masculinity as something that entails straightforwardness and confidence in my choices. I celebrate the femininity that encourages me to ask others for help and seek community, but the masculine side of me makes decisions on her own.

She is not a leader or a follower, but a lone wolf. In clothing, this is reflected in oversized button down shirts, high-waisted jeans, and boots that are good for stomping. My masculine silhouettes show skin at my neck, and are boxy and solid. My hair is pushed back so I can see what is in front of me clearly.

In my masculinity, I do not seek mystery. That is a feminine quality for me. In my femininity, I do not seek flair. That is a masculine quality for me. My clothing gets to build a story of who I am, beyond a traditional binary.

Now, as I embrace my womanhood, I get to make my own clothes and alter old ones to reveal something new about myself. I get to wear lingerie, and I get to put someone else in it. I am exploring in a way that I had forgotten how to. I am (mostly…) unconcerned about the opinions of others, because the one that matters most is my own gut reaction.

I want to wear things that make me flirt with myself in the mirror.

And I want to put others in clothing that makes them feel so deeply in love with themselves, too. Clothing can make me feel shy, coy, allusive, brash, sad, mean, assertive, and so many more things. Clothing helps to reflect the expansiveness inside of myself and the people around me.

Clothing can make a man weak with seduction, because he has never felt how snug and sexy a lace bodysuit can feel on his own skin. It can make him want to call me daddy. His experience in my lingerie affirmed my own masculinity, and the power that I connect to deep inside of myself.

The way I felt when I saw a man in my lingerie is also held up in the vintage python skin cowboy boots that make me walk tall and want to fuck shit up. I get to carry these messages, feelings, and emotions in my body, as well as ON my body.

I want to take this curiosity out of the bedroom, out of the basement, and put it on display for everyone to see.

I’m finally ready to fuck with the binary through my curiosity and clothing. And no one can tell me shit about it.

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Grace Van Der Velden

I’m curious about the spaces and places we move through, and how they shape, reinforce, or marginalize our own identities. How do we feel seen, held, and heard?