You Make Me Want To Wear Dresses

Oh hi!

Listen to this song.

Life is about LEARNING and gaining new perspectives often from other people’s experiences. Walk a mile in someone else’s shoes… or in our case, strut through the mall in someone else’s five inch black patent stilettos.

When I was younger I attended Catholic school and there was a uniform and yes, it was the plaid jumper and skirt for the girls. For boys? Well, what else are boys “allowed” to wear? PANTS.

To be fair, no one is prohibited (in the legal sense… at least not as of this writing) to wear what they choose. I heart skirts but I don’t wear them in male mode.

My sisters HATED wearing the skirt. Most of the girls in my class did as well. When the weather became colder they were allowed to wear pants and most of the girls did so as soon as they could.

I mean, I don’t blame them. It gets cold in Minnesota and I know from experience how chilly and tricky it can be walking in heels on an icy sidewalk in January.

But oh, it’s worth it.

Weather and temperature aside, I couldn’t understand why most of the girls I knew jumped at the chance to not wear a skirt when I wanted to wear one so so so badly.

(Of course, I tried on my sisters’ uniform when I had the chance and it was EVERYTHING I had dreamed of. But I digress.)

Growing up I was good friends with a girl who had a huge impact on THIS side of my life. She was the one who first told me what crossdressing was. I didn’t know there was a word for people like myself. It is no exaggeration to say that no word in any language has had the same impact on who I was, who I am, and who I will always be than the word CROSSDRESSER.

The second thing she said that had a huge effect on my perspective on femme clothes was a few months before we, along with most of our class, were scheduled to start college.

We were discussing music and I had brought up the aforementioned song. I had heard it on the radio recently and I had speculated on what it meant.

Do you remember those days? The moment you realized that not everything was literal? That songs and creative works often had subtle meanings? Metaphors, symbolism… they were everywhere and it was fun to interpret what the artist or novelist or musician was actually saying… when it was different that than the words they were using.

My friend glared at me as if I was the most clueless person on the planet. You know that look. Like, only a boy could be THIS stupid. She patiently and kindly explained that the character in the song must really like someone if she wanted to wear dresses for them.

I was like… so?

Again, she patiently explained that most girls HATE wearing dresses. Dresses, skirts, every heel that I longed to wear were not things most girls liked wearing. Essentially, her perspective was that the character in the song was willing to tolerate wearing a dress for the person she was crushing on.

My mind was blown.

I had NO idea that so many girls hated wearing dresses and skirts. Over the years I heard this same thing. Of course, some girls heart skirts and stilettos but the majority of them? Not so much.

Please don’t misunderstand me. This is not meant to throw shade at girls who choose not to wear dresses or other items that WE want to. Everyone should have the freedom (in a societal sense) to wear what they choose. A girl can wear whatever she damn well pleases. After all, they fought for this right.

As my relationships with cis women matured over time, I had new glimpses into the reality of their lives (particularly their wardrobes). Most girls I lived with, be it a roommate or a girlfriend or my wife, took off their bra as soon as they could. They couldn’t wait to change out of their skirt into comfy clothes. Most girls hated bridesmaid dresses even though I couldn’t get enough of mine.

Teenage me wasn’t able to comprehend that. But grown up me? Yes, I get it. I can even relate. As much as I love my corset and how it makes me look, there is a certain feeling of comfort when I unhook and uncinch it. I have Very Cute heels and Very Sexy stilettos… but my feet do feel better when I slip (or unfasten) them off.

When I am en femme I am always in heels and a dress (except for a few outfits I modeled for En Femme or when I took that yoga class). It’s inconceivable for me think of Hannah in slacks.

But being en femme is a treat for me. It’s fun to dress cute. It’s a wonderful break from my boy life and my boy clothes. I know myself well enough that if I were to transition I would wear dresses or skirts every day… for a while. I have lazy days in male mode and I know I would have lazy days en femme. I know there would be days I would opt for leggings and a t-shirt and minimal makeup.

Time and experiences (both my own and listened to) have shaped my perspective on many things, especially clothes.

But I still dance to this song.

Love, Hannah

7 thoughts on “You Make Me Want To Wear Dresses

  1. All this talk about dresses by you and Kandi made me go out and get a dress, my second dress. My first was a LBD cocktail dress from Victoria’s Secret, remember when they also sold clothes. The new dress is a body contour mini from Express. It’s a medium and fits great, but it “shows off” the lack of a rear end. I also have two skirts, one faux leather.
    In “male mode” I blend women’s fashion into my everyday look, including heels, pants/leggings, tops, and jackets.
    The trouble is I have no place to wear dresses, I have only gone out en femme a few times at Halloween. Maybe if I had someplace to wear them to I might wear them more often.
    I admire that you are able to enjoy life in a dress.

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  2. I’m not sure but maybe cis women or girls don’t care for dresses and skirts as the connotation has been for so long that it makes you look and feel weak.
    I think as a society we have looked on femininity as weak and many cis women don’t care for that
    It’s just a thought but hey that’s likely the fault of this male dominated society
    Who knows

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  3. You know what they say, a woman can’t wait to get home to take her heels off, a crossdresser can’t wait to get home to put their heels on….

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  4. Experienced a pencil skirt once with a short hem and loved the experience. Learning to sit with knees closed and not show the underwear was quite the challenge. Loved walking about and feeling thighs rubbing together really gives your spirits a lift.

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  5. I went to Catholic school as well. I still long to go to school every day in those plaid skirts. The girls in our school never were not allowed to wear pants only the skirt uniform. I still remember not being able to concentrate because I watched the girls and wished. Unfortunately for me it was light blue shirts and dark blue pants every day.

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