I’ve been getting a lot of emails recently from people asking what does their crossdressing mean.
What they want to know is WHY they crossdress and what their crossdressing means about their sexuality.
No one, especially someone like us, can be neatly or satisfactorily explained or described in a sentence or two. Human beings are complex, multi-faceted people and there are rarely words that accurately explain who we are and why we are.
But let’s give it a try.
I don’t expect everyone to agree with me, and that’s okay! The internet is filled with different experiences, opinions, and perspectives. I try to break complex things down (such as gender identity and wardrobe preferences) to something simple. My explanations can often be oversimplified and usually lead to more challenging and soul-searching introspection. I can also only offer perspectives on my own life with the hope that it might help someone else.
That being said, I don’t know WHY someone crossdresses. I know why I do. I wear “girl clothes” because I am transgender, or, more specifically, bi-gender. I identify as transgender because of my broad definition of what being trans means (at least to me). My definition of being transgender is something that is typically associated with a gender that is different than they one they were assigned to at birth. I admit my definition of transgender covers a LOT of territory and I don’t expect all of us to agree with it. And that’s okay, I am not trying to convince anyone here. I believe people should wear what they want, no matter which gender the clothes are designed for. This…., well, it’s not enlightened exactly, but this perspective de-genderizes clothes. Why should only girls wear leggings and nightgowns and cute panties? Anyone should be able to wear what they want, and anyone CAN.
Being transgender doesn’t mean surgery or hormones or transitioning. At least not to me. I acknowledge that being transgender might mean that to someone else and that’s okay! I am not here to tell anyone that their perspective and opinion is wrong.
So why does someone crossdress? Because, well, they want to. There’s something about dresses or stilettos or makeup that simply draws their attention or curiosity. There is something alluring and enchanting about lingerie or a little black dress. A man might be attracted to a girl because they are wearing a leather miniskirt and fishnets, but for someone like us, we might also want to WEAR the leather miniskirt and fishnets. I know I do, and I do. Let’s think of this as a door, in a way. This new door is open to someone like us, the door that connects noticing the girl in the skirt and (opens the door) wanting to wear what she is wearing.
I think (and again, I understand that we all have different opinions on this) that crossdressing is a facet of being transgender. Wearing “girl clothes” might have something to do with your gender identity, it might not. I think for me it has EVERYTHING to do with my gender identity. I am ALWAYS wearing “girl clothes”, even in boy mode. I sleep in a nightgown, when I wake up in the morning I wear panties and leggings. I wear “girl clothes” in boy mode. I wear nighties, panties, femme jeans, and leggings because they are comfortable. I don’t care (but I love that they are) that they are “for girls”. You could invent the most comfortable, softest pair of leggings in the world and some men would still refuse to wear them, even in private, because they are “for girls”. Not someone like us. We don’t care that they are for girls. In fact, since they are for girls some of us want to wear them even more.
Wearing girl clothes and identifying as a crossdresser has NOTHING to do with your sexuality. Wearing a dress doesn’t make you gay. Just because you sleep in a nightgown it doesn’t mean you want to sleep with a man. That being said, some crossdressers like to be with a man when they are dressed in lingerie or anything else. And that’s cool. You do you. What I wear has a lot to do with my gender identity, but it has nothing to do with my sexual identity. Clothes do not turn someone gay or bisexual. If you want to be with a man when you are dressed, it (in my opinion) likely means you also want the same thing when you are not dressed.
Let’s go back to the door metaphor. For some men the idea of being intimate with another man is not appealing to them at all. But when they dress, their inhibitions fall, we are more in touch with what we want… and that door opens a little. Suddenly being with a man is a little more… attractive when someone is dressed in stockings and lingerie. But the lingerie didn’t magically change their sexuality, they are just more in tune with their desire.
Again, I don’t expect anyone else to agree with me. These are broad perspectives and of course, strictly my own opinion. Like I said earlier, people are complex and what might describe one person can’t necessarily describe someone else. My point in all of this is to express that wanting to wear girl clothes doesn’t necessarily mean that one wants to BE a girl. I don’t want to be a girl full-time. I like going back and forth between genders. I like wearing girl clothes in boy mode. I have no desire to be with a man, regardless of the gender I am presenting as. So just in case you need to hear it. wearing a dress or a bra or painting your nails doesn’t mean your gay or bi. I mean, you MIGHT be and that’s okay! But wearing panties or boxers (ick) doesn’t change your sexuality.
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Love, Hannah
Hannah McKnight 
i totally agree. thanks so much for expressing your feelings i always enjoy
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Well said!! Panties and leggings are just so comfortable
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Yes well said Hannah, I too wear lots of girls clothes, wither I’m in full makeup and wig or not.
To me girls clothes are just more comfortable to me and yes I too and trans, gender fluid, bi gender or whatever
I am who I am and I’m totally comfortable with that.
People just need to get over the fact that somehow wearing or presenting ourselves differently is somehow a threat to them
We are people and just want to live our lives and express ourselves
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I love wearing bras panties ,tights stockings ,the list goes on ,I think it helps having a small frame ,but what the hell wear has you want to wear,but how to do you these corsets on !!!
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Hannah
Well said wear what you want to wear I identify as gender fluid, bi gender, I go back and forth between boy and girl. I just love to put on a pretty dress and do my nails and wear makeup 💄. Who care wear what the f#*& you want to wear.
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Wait, wait for a moment here. Cross dressing is something that a person does for any number of reasons, as Hannah regularly points out. Regardless of why someone crossdresses, the clothes that are selected as the cross dress clothes, are clothes that are typically associated/meant for the opposite gender. Typical male to female cross dressing might be about simply wearing comfortable clothes, (sure, leggings are comfortable) but I am going to guess that for many, perhaps most, male to female cross dressers the clothes that are selected are chosen precisely because they are typically worn by females. I don’t want to simply be wearing comfortable clothes, because if that was so, then sweat pants and sweat shirts could be a top choice (yuck, for sure). I like to wear clothes that are expressive of and connected to the feminine world. Girls clothes make me feel connected to the feminine side of the universe. Girls pants are so nice because they are girls pants. Onward for us all!
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For me, wearing ladies clothes gives agency to my “feminine side” of my brain/personality. For me, it is important that the clothes are gendered. Like, if given a choice to wear a men’s kilt or a pair of ladies pants, I will chose the ladies pants.
My feminine side of my personality wants to be expressed, and wearing ladies clothes is the best and easiest way to achieve that.
I didn’t understand my crossdressing feelings (the whys) until I understood that my mind has a feminine side. Once one accepts (and this is VERY HARD) that they have a feminine side, things get more clear.
– Christina Cross
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I’ve spent almost 25 years wrestling with this question, and only have a few answers:
1. Guys clothes… um… suck! They are boring AF!
2. I can better express myself in a cute dress, makeup, wig, and heels than I do in pants and a shirt.
3. I don’t just like seeing beautiful things… I want to be beautiful myself… even if I just feel beautiful. No one else has to think I’m beautiful… just me.
4. It’s who I am. I (personally) am not just content with wearing a dress… anyone can do that with minimal effort… I want to be Alicia… I am Alicia… and she has curves, long hair, and is… well… a woman!
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Well said. Reading this piece I couldn’t help but think about how very silly and unfair it is that even have to consider ourselves “different” because of the close we want to wear. If we were cis gendered women no one would bat at eye at us for going from a cute dress to a pair of work overalls. But because we were born genetically male we have to explain ourselves and live with judgement and disapproval. It’s so annoying that our society has pushed us into this arbitrary box.
Love your writing Hannah but even more I love your attitude about dressing and being yourself. You’re an awesome role model and a beautiful person. Some day I hope to find the courage and strength to be as open about myself as you are.
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As you say it is a full spectrum and I doubt there are any generally applicable reasons. However small children like to dress as characters that they admire or emulate, princesses, astronauts, etc. and wanting to emulate the things that we find appealing or attractive is surely the whole basis of fashion. For some of us the fashion that we find attractive and appealing is that of the opposite gender to the one we have been assigned. I think fashion choices are also a spectrum, goths, lolitas, cosplayers all are making clothing choices to that are not mainstream fashion but they are doing it presumably because it is what appeals to their mental image of how they should look and the people and communities with which they want to socialise.
For me this is a deeper explanation of “why”, in life there are a wide variety of options and some combination of the way our brains develop leads us to like some things more than others. When we are young we might see a particular group having more fun or doing more of things we would like, conversely we might also feel like we don’t fit in with the social groups and activities that are assigned to us at an early age. Most of the things that we are attracted to and enjoy are not of any consequence because they are within social norms but some things break with social conventions and it then becomes a struggle between what we desire and what society expects.
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I must admit I would really love to tell my wife that I would like to wear dresses and skirts all the time ,but she is of the strict Catholic attitude! I try to st away with ad much as I can. Being a man I have tried to be more manlyish but I have not succeeded ,so with .my small frame and as I feel I prefer female stuff .In fact I have a enter female figure than my sister in law!!But one thing my wife can’t complain about are my pearl earrings that O wear.
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