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How to play with gender - 7 tips that may help you get started

Updated: Sep 20, 2022

"A critically important component of wholehearted living is play!"

Brene Brown, The Gifts of Imperfection

A brown skinned human looks straight at the camera while wearing a lioness mask. They are wearing their hair in braids with a brown beanie and a multicolored sweater. They stand in front of an alter with images and sculptures of cats.
Nijlan "Wearing this mask I embody an essential part of my soul. It helps me to conjure magic and blessings that otherwise would not be. And is distinctly ungendered."

Sometimes it feels like spaces created for trans and gender non-conforming people can be so serious! While I respect and honor the need for educational spaces and therapy groups, I also see the importance of spaces that prioritize play and fun! There are many books, articles, and theories written about play, but I will focus on two reasons why play is important:

  • Play can help us explore who we are and what we want - Children learn primarily through play. I believe that many people (especially trans and gender non-conforming people) naturally play with different clothing, activities and expressions. Sadly, our culture often tells children they can only play with certain things, arbitrarily labeled as "boy things" or "girl things". This limits authentic expression and tells children that they need to change who they are to fit in. Luckily, we can reclaim this ability later in life by relearning how to play! This can help us to tap into more authentic ways of living and expressing ourselves.

  • Making space for creative joy helps to build resilience - we all have our own challenges in life and finding activities that tend to our nervous system can help us to be more resilient when challenges arise. I have been making a personal practice of prioritizing joy and playfulness as often as possible. It doesn’t make the hard things go away, but it allows me to rest and show up more resourced.

A Latina drag queen bites her pinky and looks up to the left. She is wearing a bra and top that covers her shoulders and matching gloves with flames. She also wears elf ears to play with gender.
Drag performer Beatrix Jean Krenwinkel

Black drag kings, pretty boi drag, stand on stage. The front performer Pretty Rik E wears a white baseball cap and white blazer and has a fake beard on. He accepts money from an audience member.
Rik E King from Pretty Boi Drag

7 tips for how to play with gender:

1. Halloween & Costumes:

For many people, Halloween was the first time they allowed themselves to play with gender! This can be impactful, whether it’s with a small group of people, going out to a party, or even dressing up alone. There is also a lot of potential inspiration for exploration and weirdness: aliens, celebrities, animals, concepts, etc. This also applies to rocky horror shows, conventions, and other spaces where costumes are the norm.

Looking back, Halloween was the first time I publicly played with gender when I dressed up as a sloppy boy from the rival school. Even though I didn’t know anything about transgender identities, I did secretly know I felt an affinity towards “boys clothes” (I don’t believe clothes are limited to any gender but at the time these clothes felt off limits because of cultural norms). I remember looking in the mirror in certain clothes and feeling a spark of recognition in myself, thinking “this is nice, but can I wear this in front of other people?” Dressing up on Halloween was a low stakes way to try it out.

Years later when I was out as queer but unsure if I identified as trans, I had another significant Halloween that helped me to explore other aspects of my gender. I was considering changing my pronouns and taking hormones. My roommate had the idea of dressing up as a sexy Vincent Van Gogh (which felt like a great way to play with gender norms!). I drew on a beard with eyeliner pencil, wore a painter's smock, fishnets and heels. I liked being able to play with seemingly contradictory gendered clothing and express parts of myself I had been hiding. It allowed me to notice how it felt to have a beard and be called he pronouns. This night was affirming and also helped me to make decisions about next steps in my gender transition.

Even if you are not considering hormones or a change in pronouns, playing with gender can be fun for anyone! I believe our culture would really benefit from releasing rigidity around gender norms.

While gender bending is often more socially acceptable on Halloween, if you are going out I recommend going with a friend you trust and having a plan for physical and emotional safety during and after the event.

A white queer person gets inspiration from Vincent Van Gogh to play with gender. They are wearing a painters smock, fishnets, and heels. Their ear is wrapped in a bandage and they are holding a paint palette. They are jumping up and down with excitement.
Rainbow dressed as Sexy Vincent Van Gogh for Halloween

A gay white man cross-dresses as a woman wearing a curly black wig, a leopard print shirt, and tiger print pants.
Nolan "my friend who enjoys the freedom and exuberance that comes from playing with crossdressing"

2. Drag:

While the current mainstream view of drag is related to a very popular TV show, that is only one aspect of what drag has to offer! Historically, you find drag spaces being a place of refuge and self expression. There, many of our queer and trans ancestors bucked social norms and celebrated queerness. Of course, you cannot talk about drag without mentioning the Ballroom scene, where Black and Latinx LGBTQ individuals shape culture as we know it. In fact, drag is extremely diverse and comes in every shape and form. An often overlooked aspect of drag culture is the rich history of drag kings. We also find drag performers who don't fit into the king/queen binary and fuck with gender.

Sometimes it can feel like the standards for drag are very high with expectations of perfect makeup and costumes. The beautiful thing is that you don't have to participate in drag spaces that don't feel right for you (or you can wait until you are ready). Remember that you don't have to do it perfectly, there is no one way to do drag, and there are ways to find or create spaces that are welcoming to you. A great place to start is doing drag and taking personal selfies or playing “dress up” in a supportive group of people *ahem like the GENDERPLAY workshops in my events page*.

Personally, drag has had a powerful impact on my life. Early in my transition, I was working through a lot of shame around my gender presentation and other people's discomfort. I had friends who performed and got me into the scene. There I explored aspects of my gender identity that I often felt pressure to hide in daily life. I did a few shows with another transmasculine person where we performed as gay cowboys and revealed glittery ace bandage binders (not recommended for daily use). I had another performance to Frank Sinatra's song My Way, where I subverted 1950's gender norms by starting in a suit and changing into a frilly cleaning outfit. The beauty of these performances was being celebrated and cheered for things that society had often shamed about me.

Black drag king, Pretty Rik E, stands on stage with arms outstretched and lights in the background.
Pretty Rik E from Pretty Boi Drag claims the stage.

White drag queen Venus Black wears a sleeveless short blue dress, blue makup, and wears a clutch that looks like a vulva.
Drag performer Venus Black rocks a vulva clutch

White drag king looks at the camera with curly blond hair and sparkles on their face.
James Fondle (my old drag persona)

3. Art and Visualization:

Art can be a powerful tool for play and exploration. This includes creating art that explores different types of clothing/attire, feeling into medical and social transition decisions, and creating a vision for how you authentically want to live in the world. If you don't feel confident with drawing or painting, other options are doing photo shoots, free-writing, or collage. At the bottom of this post, there is a link where you can sign up for my mailing list and receive some journal prompts to get started playing with gender! Your responses don't need to be in writing, you can draw, take photos, sing, etc.

When I was debating taking hormones, I used art to help me decide. First I read about the effects that hormones would have on my body if I took them for a few years. Then I used drawing: I sketched a messy drawing of myself having those physical changes and noticed what I felt in my body (fear, excitement, relief). I then drew myself without those changes and compared my notes.

Freewriting was another helpful activity, taking time to write from the perspective of a future me who had made these changes. These exercises can help with making decisions about medical and social transition, but they can also be used to tap into different parts of ourselves that may want to be seen. The activity itself can be helpful even if it doesn’t lead to a big decision down the road.

A sketchpad on the ground with many squiggly lines and multicolored shapes.
You can also express yourself with simple shapes and colors.

A Black, femme, non-binary human uses an online filter to play with gender. This person looks up at the camera with a beard and bushy eyebrows created by the filter.
Tabitha shows us another easy way to explore can be using filters on social media apps.

A white non-binary person wears a red lip, white and black eyeliner, a feather earring, necklaces, and bare shoulders to play with gender.
Alexis shows off their makeup and hair style

4. Get inspired:

A fun way to get started is to get inspired by other people. Sometimes our brains like to ease into new experiences, so looking at images or reading stories can be an amazing baby step towards creating more space for gender play in your life.

One way to do this is to play with gender around other people in a supportive environment, you can also save accounts and images for moments when you want an extra bit of inspiration. In this blog post, I asked friends for images that might help get your inspiration wheels turning, but there are other places to look! Think about what inspiration feels most exciting at this time: gender fluidity, certain fashion styles, makeup aesthetics, trans models, etc. Then think about how you want to take in that information, the internet is a great source of inspiration, but it also has potential for running across transphobic or hurtful commentary. Some ways to avoid this are saving specific websites and accounts. Social media often leaves room for comments, so it can help to decide in advance if you will read them and having a self care plan for anything that may be triggering. Other options are finding books, zines, tv shows, events, printed photographs, and art that feels inspiring. It can be helpful to collect these resources when you have more support/energy so they can be ready for times you might need them.

While looking for inspiration, be careful to try and not get caught up in comparisons with other people! If you do find that happening, remember that it is very likely that even the most fabulously confident person has also doubted themselves or struggled with self criticism. Just because your inner critic has a lot to say, doesn’t mean that voice is telling the truth! Working with compassionate meditation and therapy can be helpful to address comparisons that come up.

A white man wears a black and white polka dot top, yellow nails, and a silver and black cat mask to play with gender.
Nolan wears a silver cat mask and yellow nails

A non-binary, femme, Black person wears shoulder length curly hair, eyeliner and light eye-shadow, a red lip, a black necklace, and a houndstooth jacket.
Tabitha wears makeup and a houndstooth cardigan

5. Trans Ancestors:

Looking to trans and gender non-conforming ancestors can be another great source of inspiration. Even though there has been a consistent effort to erase our stories, we have ALWAYS existed. In fact the current western cultural attitude towards gender is very new (see Alok Vaid-Menon’s book Beyond the Gender Binary for more of this history).

If you have a spiritual practice, working with resolved trans and gender non-conforming ancestors can be a great source of support and inspiration. Even if you are not ready or interested in ancestral practices, there can be a lot of benefits to reading about and learning from those who have gone before. Some great sources of inspiration are: Sylvester (the singer), Marsha P Johnson, Sylvia Rivera, Lou Sullivan, Leslie Fienberg, Gladys Bentley, and many more. You may be interested in exploring ancestors from where you live or that share your own lineage and culture.

A marker drawing of Marsha P Johnson wearing a flower crown which is decorated with glitter.
A drawing of Marsha P Johnson I made

6. Neurodivergent people can play with gender!

There is a lot to say about this so follow my blog for future posts! Let me know if there is a topic you want more information on. Everyone is different, so I am just offering some considerations.

If you are Autistic and/or have sensory processing differences, keep your sensory needs in mind while playing with gender. Consider what clothing and makeup feels good on your body. If you want to wear something that is uncomfortable to you, perhaps you can layer more comfortable clothes underneath or only wear that item for a short period of time and do a photo shoot. If you have a sensitivity to noise, consider playing with gender virtually or in a small group. Earplugs or headphones can be helpful in loud spaces.

For people who like routines, consider ways you can create safety while playing with gender, maybe first incorporating it into something you and then doing a familiar activity afterwards to build safety around this new activity.

I personally can deal with "all or nothing thinking", which is often correlated with Autism and Neurodivergence. It can be helpful to remember that little actions are powerful and change happens one baby step at a time. When we celebrate small actions, that helps us to create confidence in taking other steps in the future.

A nighttime photo with an infinity symbol drawn with light in front of a starry sky.
The infinity symbol is commonly used to depict the autism spectrum

7. If it feels scary:

If all of this feels scary, you are not alone! Just opening this page and looking through it can be a big deal! If you notice yourself feeling overwhelmed in this moment, I recommend taking a break and doing some self-soothing (stretching, eating a snack, drinking water, shaking, etc.). You do not have to instantly jump into the most scary form of gender expression in this moment, instead you can celebrate yourself for taking a risk and allow yourself to mentally "digest" this information for as long as you need.

On the other hand, if you are feeling some fear/nervousness, but are also feeling excited/curious/interested, that's okay too! Fear and excitement can feel very similar in our bodies. We also may have a conditioned fear response that comes from past life experiences. It can be helpful to remind yourself that fear is natural and you are now able to try new things.

You do not have to do this alone, trying new things in a supportive space or working with a gender doula can be really helpful for working through the nerves.

A queer Filipino woman looks up at the camera. She has short hair with a fade on the sides and is wearing a leather jacket.
Alex wears a short fade and a leather jacket

A white gay man wears a bright yellow ponytail wig and twirls it with both hands.
Nolan's look is a reminder to have fun!

Want to learn more?

Sign up on my email list to receive free journal prompts to get you started!


Thanks to everyone who donated an image to this blog! To learn more:

(not everyone shown had a website they wanted to share)

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