Man in a Dress

Sometimes I feel like a man in a dress.

And it’s almost always because that’s how I feel like I look.

It takes an insane amount of courage (among other things) to go out into the real world en femme.  To leave your home in full makeup and a cute dress takes an amount of bravery that is incomparable.  If you’ve ever been out in the real world, then congratulations.  I know how hard it was.  If you aren’t there yet, then don’t be hard on yourself.  It’s the most difficult thing I’ve ever done.  

What I find difficult is leaving the house when I am still partially in male mode.  At least when it comes to my face.  If I am doing a photo shoot I will always book a makeup appointment for the day.  On days like this I spend the morning getting my corset tightly cinched, my forms and pads in place, and getting dressed.  I then leave the house and make my way to my appointment.  I try to plan my morning so I don’t have to run any errands before my appointment, such as getting gas because I hate, hate, hate doing anything before my makeup is done.  But sometimes it’s unavoidable.  This past weekend I was on my way to my appointment when I had to use the ladies room.  I didn’t think I could wait until I got to my appointment so I decided to run into a Starbucks.

I got there, parked, and sat in my car for a few minutes working up the courage to go in.  At the time I thought looked cute (well, my outfit was cute) but my face was MALE.  Like, full on MALE.  I look SO MALE before I have my makeup done.  Once my makeup is done and my face is contoured, my foundation is set, and my eyes have more drama than a soap opera I feel and look more femme.  But before that my reflection shows a middle age man wearing a long black wig.  It’s devastating, it’s heartbreaking, it’s… it’s a lot of things.

Please bear in mind that I don’t feel that way about my reflection when I am in boy mode.  I don’t hate how I look in boy mode, not at all.  But I don’t want to look like a boy when I am en femme.
It takes a lot of courage for me to go anywhere public when I am en femme before a makeup appointment.  But I had to.  I put on a mask to hide half of my face and strutted into Starbucks.  The strut was a lie, I didn’t feel like strutting but sometimes you have to fake confidence.  I popped into the restroom, cringed at my reflection, and bought a bottled water on my way out.  

And that was that.

I went to my appointment, got my face done and was feeling about 500% cuter.  Now that my makeup was done I could properly assess how I looked.  And I felt like a man in a dress.  Or more accurately, a man in a skirt.  I rarely wear skirts.  When I am en femme I am almost always rocking (or trying to rock) a cute (or sexy) dress.  I feel confident, I feel beautiful in a dress.  But a blouse/skirt combination?  I rarely feel cute.  I felt the top I was wearing made me look too mannish.  It wasn’t really cut in a flattering, feminine way despite the small ruffles adorning it.  I felt like I was wearing a simple tank top, which is essentially what it was.  In my head the outfit looked cute but on me?  Ehhhh.  Despite my stilettos, the skirt, fake eyelashes, my amazingly realistic breast forms, and my bright red lipstick, I felt like a man in a skirt.  

Isn’t that funny (and heartbreaking)?  My makeup, my heels, my skirt… almost none of that mattered compared to how I FELT.  Shannonlee said I looked cute.  I posted the outfit on Twitter to get some feedback and I had some nice comments.  But none of that mattered.  I didn’t feel cute and nothing would change that.  

This feeling lingered with me for the entire day.  No matter what I wore, no matter how cute or sexy or feminine my outfits were I couldn’t shake the feeling.  People can be cruel to our community, but we can be cruel to ourselves. 

Dysphoria is a real thing and it can hit us from out of nowhere.  Most of the time I like how I look or at least my confidence is high enough to overpower any negative thought or comment but no one is immune to the seemingly out of the blue voice of not being cute enough.

So the question is what do we do when this happens?  You kind of have to power through it.  Sometimes this works, sometimes it doesn’t.  Just understand that these negative thoughts will happen and will always catch you off guard.  Sometimes I can bounce back from these thoughts and feeling.  When I changed from the aforementioned outfit into a super femme dress, well, I felt cuter, although the dysphoria was still lingering.  Sometimes these thoughts can’t be shaken off when we are en femme.  And that, well, that sucks.  You look forward to getting dolled up and spending the day en femme and WHAM!  Dysphoria.  It’s like looking forward to a road trip and getting four flat tires.  Or the heel of a stiletto snapping off in midstride. 

It’s hard not to, but you really can’t let it dull your sparkle.  If you can’t bounce back from this while you are en femme, it’s okay.  Dysphoria doesn’t really MEAN anything.  It doesn’t mean you aren’t beautiful or your outfit isn’t cute.  It’s just a small, cruel voice or a negative emotion that we are paying attention to when we shouldn’t.  We can choose what or who we listen to, but I do know (I promise) that this is easier said than done.  If these thoughts, this voice lingers for the day until you go back to male mode, don’t let it discourage you from your next time out en femme.  More than likely you will feel cuter the next time.  You can almost always chalk up dysphoria to just having an off day.  I mean, we have bad days at work but we still show up the next day, right?  

But I do get this is all easier in thought than it is in practice.  I felt not-cute for most of the day, and that emotion stuck with me even after I went back into boy mode.  Shannonlee sent over some test shots later that evening and the photos looked a zillion times better than dysphoria said they were.  My thoughts weren’t really based on anything tangible or anything real.  I was having an off morning, not every outfit looks cute on everyone.  

I feel better about the day now than I ever did during the day itself.  My confidence took a severe and lengthy beating that day.  I was feeling frustrated by, well, everything that day until I realized (much later) that although the outfit probably wasn’t right for me, most of my negativity was all coming from dysphoria.    

And like having bad day at work, we wake up the next morning and we tell ourselves that today will be better.  And it almost always is.   

Love, Hannah

10 thoughts on “Man in a Dress

  1. Yes, we ALL know that feeling! And yes, it does take a lot of courage to step out into the world enfemme, especially when you’re straight and most of your friends and neighbors only know your guy side.


    1. Honey, what is “especially when you’re straight” supposed to mean? Presenting to the public always requires courage, regardless of sexuality…but maybe it is harder if you’re “straight”🤣😢


  2. Oh so many times have I looked in that mirror, makeup and all as I’m about to go out the door and think oh my goodness, I will be read immediately and wonder what am I doing
    Then I think, but this is me that person looking back at me is who I am. Sure I have a male build but I am a trans girl and I feel those of us that can and do go out each time we are seen our society can recognize we are just people like anyone else and we are pretty harmless
    It’s ok to doubt but just be you and find your happy place


  3. A couple of days ago I decided to get something from a drivetru and I said: I want to go in a dress but I’m too lazy and hungry to do make up and such, since I wasn’t going to leave the car the car anyway I went for it, I decided to put the shortest and tightest dress I have and I love it, the window lady didn’t even cared that a man in a dress came by
    I might do it again 🙂


  4. You my also have a reverse problem, you have your male ‘hairy caterpillars’ of eyebrows waxed, take to much off and tongues may wag


  5. When I look in the mirror I try not to see a man in a dress but the image of who I am. I say that there are 360 degrees to my personality and I enjoy all 360 of them. I gain so much courage to step out I the world from reading your stories. Thanks


  6. This is another excellent essay Hannah! The internal feelings that dressing en femme allow, inspire, and cause are both wonderful and joyous and disappointing and frustrating. The feeling of absolute joy, delight, is one that I am guessing, hoping, that all who dress en femme know and revel in. The feeling of disappointment and frustration that, as Hannah describes so well in this post, often overwhelms and tints the day blue. What to do? Hannah’s advice is spot on: keep on rolling for the sun will shine again. Do what you enjoy and be as happy as you can. Onward!


  7. I think that the cliched trope of “ man in a dress” has been common in theatre since Ancient Greek times. Once he is “unwigged” and revealed as a gender imposter everyone has a good laugh and goes home. This idea that a man would only be feminine as a joke or to mislead others is ingrained in our culture. Every time I go out proudly presenting as a man who is open minded enough to admit that enjoying expressing the femininity that I know is inside of me, I’m not just having fun but I’m helping our society to grow. Every single one of us sees the world a little differently, and we all need to recognize that.


  8. Hi Hannah, I ❤️ you & all your advice, you’re so helpful to all us girls out here & you were so helpful to me in the beginning. I’m always looking forward to a new post.
    I think you’re to hard on yourself sometimes, I’ve seen many of your pictures from your photo shoots & girl I think you look fabulous!! It’s all about looking beautiful & I think you pull that off without a problem. You’ve written many, many times about how it’s not about passing, which we will never completely do. I know I will never completely pass & I don’t care, I do my best to look the best I can & when I look in that mirror, I am Diane & beautiful. It doesn’t matter what people think, there are always going to be haters & the people who don’t understand us, but that shouldn’t stop us from being who we want to be!
    So go easy on yourself, you ARE beautiful & you are an inspiration to us all.

    Sincerely, Diane


  9. I often wonder if we place too much emphasis on passing. I’ve only been out once before, dressed up. I went to a mall for some femme shopping. I sat in my vehicle for a short while outside the mall, then built up the courage to go inside. Once inside, I loved the thrill of being femme and out and dressed and didn’t care if I didn’t pass. I was hoping I would walk into someone I knew and that they recognised it was me. My secret would be out, but at that moment I didn’t really care.


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