Our gender identity is a journey, and like all journeys, we change throughout it. We are not the same at the end but that’s usually the reason for the adventure… We SEEK the change. We WANT the change. Perspectives change, we let go of things that at one point consumed us, and our priorities realign.

All of us are on, or have already finished, this journey.

I imagine many of us can look back on where and when this all started and appreciate how far we’ve come, even if it’s just the tiniest progress made with the tiniest baby step. We take those early tentative steps in kitten heels before we are strutting in five inch platform stilettos. You could draw a line (it would not be a straight one as all adventures have detours and backtracking, afterall) and you could trace my steps to when I was very young. It was a fascination for lingerie that turned something on in my head and in my heart and in my soul. If five year old me had the vocabulary at the time, I would have described this feeling as being spellbound. Enchanted.

I’ve discussed this before so I won’t dive too deep into it, but learning of the word ‘crossdresser’ was like a glitter bomb exploding all over my world. At the time I understood it was a term for “men who wear girl clothes” and well, it’s a little on the nose but if the shoe fits… When I was older I learned how entwined the word was with kink and fetishism (not that there’s inherently anything wrong with that). Although there wasn’t a sexual element with who I was, I still identified as a crossdresser because it was the only word that I knew of.

In my early thirties I started to wear clothes beyond lingerie and adopted a femme name and I realized that all of THIS was more than just clothes. I didn’t feel that I was “a man who wore girl clothes”. It felt bigger. It took a little time but eventually I gravitated towards identifying as transgender. I was reluctant to adopt this as I understood at the time that The T Word was for people who had, or were in the steps of transitioning. I wasn’t heading down that path but a friend shared her definition of it. She explained a transgender person who feels that they don’t really fit within the expectations and standards that society has for the gender they were assigned at birth.

Again, a little on the nose, but that was me.

She said the term was more or less an umbrella term and there were other, more nuanced terms that fall under the transgender rainbow. Terms such as non-binary, gender queer, agender, bi-gender, and yes, crossdresser. Essentially she felt that someone who identifies as a crossdresser could also identify as transgender.

If they wanted to, of course.

Terminology in our community is a beautiful mess and we all have different perspectives and opinions about what all of these words mean. I have no interest in appointing myself as the Grammar Bitch and enforcing all of these (arguably arbitrary) definitions but I get frequent emails about all of this. Several times a week I’ll get an email from someone that says something along the lines of “I’m a man that wears ________. Does this mean I am __________?”.

My reply is almost always along the lines of “well, if YOU want to be.”

We can choose how we identify. For some of us, a term is restricting and pointless. For others, it’s reassuring. ‘Crossdresser’ was very reassuring to me when I was younger. I felt… seen… knowing that there was a word for “a man who wore girl clothes”. I felt less alone knowing that there were SO MANY men who wore girl clothes that there was a word for us.

We are all able to define for ourselves what these terms mean. Many people disagree with my definition of ‘transgender’ and that’s okay. Again, not trying to be the Head Grammar Bitch. But let’s chat a little about what crossdressing can mean. CAN is the operative word. Again, I am not trying to ultimately and definitively anything, but rather this is meant to empower and reassure anyone that is a little lost on their journey.

When I say “reassure”, my goal is to let you know that you are not alone in what you feel or what you wear. When I say “empower” I want you to know that you shouldn’t let ANYONE, especially me, influence how you identify, IF you CHOOSE to identify as anything at all. After all, if you are a man that wears girl clothes, wonderful. You don’t HAVE to be anything else. You can simply be a man that wears girl clothes if you wish. There’s no requirement to attach a term to who you are.

So, let’s talk about how crossdressing is a spectrum.

I felt less alone knowing there were SO MANY men that wore girls clothes that there was a word for us.

Although WHAT crossdressing is will have a zillion different opinions, I think we can all sort of sort of and broadly and maybe agree that crossdressing is when someone assigned male at birth wears something that society typically associated with someone who was assigned female at birth. And yes, all of this starts at birth. People freak out when a baby boy has a pink blanket.

But we already have a problem with that definition of crossdressing, lol. That explanation is only applicable to gender as a binary and gender as a social construct. Humans invented the gender binary. WE decided that boys do THIS and girls wear THAT, and so on. The world might insist that only girls paint their nails but there’s not a single evolutionary reason someone with a penis can’t have red coffin nails.

If you don’t believe that gender is binary, then crossdressing doesn’t exist at all. As I type this, I am in male mode at a Starbucks, and I am wearing a femme shirt and femme leggings. Two things that I bought from the women’s department. Sure, the barista might think that I am wearing girl clothes, but my perspective is that I am wearing (cute) clothes.

So for the purpose of this article, let’s pretend that gender IS a binary and that almost everything IS indeed for a boy OR a girl.

I am often asked how someone crossdresses and honestly the answer is so simple that it’s kind of obnoxious (and not helpful at all). All you need to do to crossdress is to wear panties or lipstick or a nightgown or a skirt or…. Essentially anything that a girl is “supposed to” or “allowed to” or “expected to” wear.

And that’s that. Ta-da! You are crossdressing. Enjoy the journey.

Again, not helpful and arguably bitchy. So, that’s not the answer I give when someone asks how to crossdress. Instead I encourage others to decide for themselves what crossdressing means to them. And yes, that does sound like an essay someone would write in high school, but the point stands. Do you want to wear panties? Do you want to wear femme jeans? Do you want to paint your nails? Do you want to get a wig and glam up from head to toe? All of that? None of that? Some of that? Crossdressing can be any of those examples… if you want it to be.

Really, it all comes down to WHAT you want to wear… and then wearing it. Ta-da! Again, enjoy the journey.

Again, not helpful and still a little obnoxious and bitchy. But what someone wears IS a very personal decision. You can wear whatever you want. Sure, the world may disagree but who cares lol. In my experience, when I am asked how someone starts crossdressing is almost always someone asking how one becomes brave enough to wear what they want. It’s all about the mental aspect. It’s about giving yourself permission (because the world will NEVER do this) to wear what you want. The person asking questions like this KNOWS that if they want to wear panties then they need to, well, WEAR panties. Again, what they are asking is how to work up the courage to do this. How does one ignore centuries of society dictating what someone is allowed to wear and what someone is supposed to wear.

The answer to these two situations is as simple as you like: You Just Do It. Just buy the dress. Just shake off what the world thinks. Or even better, stop thinking about what the world MIGHT think.

If crossdressing is a spectrum, it’s up to you to decide where to start. Your journey will likely take you to a different place from where you start, but don’t worry about that yet (or ever. Worrying doesn’t help anything or anyone). Even if you know where you WANT to end up, there’s a good chance your journey may end in a totally different place. And that’s okay. Journeys and their destinations should be organic. It’s easy to overthink all of this, and overanalysis easily leads to paralysis. We spend so much time thinking about all of this that we never start.

A spectrum implies that there is a beginning and an ending. Two opposite points. Both an extreme. If we apply this to crossdressing, then we could argue that crossdressing could be something as simple as painting your toenails. This is, in my opinion, as simple as crossdressing gets. It’s a relatively easy thing to do and painted toenails are pretty easy to hide. Buying a bottle of polish (or borrowing it from your sister) is pretty easy. On the opposite end we could say that crossdressing is still painted toenails, but also shaved legs, shaved arms, shaved body, stockings, high heels, panties, a waist cincher, a pencil skirt, a bra, breast forms, a peplum top, necklace, accessories, rings, red stiletto nails, lipstick, lip liner foundation, blush, concealer, bronzer, mascara, eyeliner, eyeshadow, false eyelashes, and a wig.

“YES! THAT’S WHAT I WANT!” You may be saying. “I WANT THAT END OF THE SPECTRUM!” Okay, great. Fabulous. But starting there will be a disaster. You learn to swim by wading into the pool under the supervision of a lifeguard. Expanding on that metaphor a bit, if you try to learn how to swim by being thrown into the deep end you’ll likely drown. When we want to do something new, we need to ease into it. We need to learn by doing.

Again, the destination is the journey when it comes to all of this. We gain nothing if we take a bullet train to where we think we want to end up. If you want to crossdress, wonderful! But starting at the end of the spectrum is probably not the way to go.

I enjoy painting and I can help but look at the parallels between that and gender presentation. Usually when I paint I have a vague idea what I want to paint or what I think it will look like when I finish, but I am almost always wrong. Which is just fine as sometimes it ends up being different, and better, than I expected. I tend to be a very spontaneous painter. What I mean is that I don’t know what the second brush stroke will look like until I’m finished with the first one. Every brush stroke is a response to the previous one. Art can usually be created by instinct, by what feels right. A painting is constantly telling me what kind of painting it will be. In a way, I am not in control. I am a conduit for what the canvas is destined to be. I can’t fight it, I can only embrace and obey it.

Crossdressing is very much the same way. Sure, you might think want to have painted toenails, shaved legs, shaved arms, shaved body, stockings, high heels, panties, a waist cincher, a pencil skirt, a bra, breast forms, a peplum top, necklace, accessories, rings, red stiletto nails, lipstick, lip liner foundation, blush, concealer, bronzer, mascara, eyeliner, eyeshadow, false eyelashes, and a wig, but you won’t know until you start your journey. You might look in the mirror after this kind of transformation but it might feel wrong. This can come off as a shock as you were SO SURE that’s what you wanted. Instead, what we really want is somewhere along the spectrum, but not at the very end of it. Although a complete transformation isn’t quite right for us, maybe being in male mode, wearing a femme shirt and femme leggings (like I am right now), feels more right. You won’t know what is right or wrong until you try everything.

It’s not unlike music. You might love classical music but not even realize it until you sit down and listen to it.

It’s a humbling thing to learn that what we thought we wanted wasn’t right for us after all. We probably feel lost, confused, and frustrated. This can be applied to almost anything in life, though. We THOUGHT we wanted a new career but when we started it we realized that it wasn’t the right fit. We THOUGHT we wanted to move to New York but all of a sudden we are two weeks into a lease and we learned that no, we actually DON’T want to live in New York.

We’ve all heard the saying about getting set up to fail. That maxim can absolutely be applied to crossdressing. If you start at the end of the spectrum we can realize that no, this isn’t right. What we thought we wanted isn’t what we want at all. Any journey starts at the beginning. Discovering who we are and what feels right needs to start small. Don’t throw yourself into the deep end.

Love, Hannah