Dressed Like a Daydream

Of course, fantasy plays a very significant part in all of THIS.  It always has.

Growing up I would dream about wearing pretty dresses.  I attended Catholic school and every single day I wanted to wear the cute plaid blue jumper and pretty black shoes.  This didn’t change in high school as I saw girls wearing so many styles and outfits.  Ninth grade was my first significant exposure to seeing girls my age wear outfits that ranged from casual to head-turning looks.  Yes, I saw what a cute girl was wearing, but I also saw what she was wearing, if you follow me.  Yes, she looked cute in that dress, but OMG how cute was the dress itself?  I was in love with the options girls had, from a summer dress to short skirts paired with Doc Martins to leggings with a simple t-shirt.  I was so, so jealous.  Of course I thought the cheerleaders were cute, but there was something more.  I dreamed about wearing the short pleated skirt.  Formal dances were the best, though.  Yes, the girls looked amazing, but again, there was something else.  I imagined how much fun it would be to wear a beautiful gown.  It almost hurt how badly I wanted to have the day she had preparing for the dance.  I wanted to look and feel as beautiful as her.

When I was in my early 20’s this world opened up even further.  I worked in an office and I saw my colleagues wear business clothes.  What a girl could wear to a meeting was just as cute as what she could wear to a dance.  Similar to wanting to wear that plaid jumper when I was in grade school I daydreamed about wearing black heels, a pencil skirt, a white blouse, and a jacket as I put on my necktie every morning. 

My friends would start getting married and weddings were almost torturous as I watched the girls in their dresses, whether the girl was a bridesmaid or a guest.  And don’t get me started on fantasizing about being the bride.  I thought about every part of her day.  From selecting her lingerie to the dress to the heels to her makeup…    

If my website has a… mission, I suppose, it’s that I want to be honest and realistic about this side of us.  Much of what I write is based on my experiences and how I handled any disappointment, frustration, or dysphoria.  I cannot tell you how crushing it was the very first time I tried on a wig.  I thought it would transform me into a supermodel.  It didn’t.  I felt uglier than ever before.  It would be a few years until I could see my potential.  Putting on a cheap wig is a lot different than selecting a quality one.  Wearing a wig in boy mode is much different than putting one on after carefully doing your makeup and wearing a cute outfit.  There’s no question that being en femme takes a lot of work and much of it is mental.  We all will feel dysphoria and hopeless, and getting over that may require us getting better at makeup (if that’s what you feel you need to do), but modifying our thinking plays a part of it too.  Shifting from “trying to pass” to embracing and celebrating how you look is HUGE.  It’s the most important part about this side of us.  

This side of us isn’t always princess gowns and French Maid uniforms.  Feeling comfortable, confident, and beautiful has much to do with what I wear.  Yes, I would feel cute in a schoolgirl uniform, but not while wandering around a mall.  My wardrobe changed over the years as I moved to cuter, everyday looks.  I suppose practical is the best word for it.  

I still fantasize about the same things that I daydreamed about while I was growing up.  I saw my sisters play princesses and I wanted to do that too.  Even now I fantasize about wearing a beautiful pink gown and a tiara.  My girlfriend in my senior year talked about how she prepared for a formal dance and how she shopped for the perfect heels, the perfect dress, how long it took for her to get her makeup and hair done… I hung on every word.  Wedding season stirs up a longing to go shopping with other girls for a beautiful dress, getting my nails done, and feeling beautiful for a wedding.  I could go on and on.  Despite the clothes in my closet and what I have done, I could name a dozen things I still fantasize about.  I want to fly pretty, I want to spend an entire day from waking up to going to sleep en femme.  I want to do a lingerie photo shoot.  Have a princess tea party.  Wear a corseted dress at the Renaissance Fair. Strut down the catwalk.  Play tennis in a short, pleated skirt.  Sit by a pool in a bathing suit.  Be a bridesmaid.  The homecoming queen.  

I have done more than I ever thought possible.  My life is amazing.  If I never do more than what I have done than I will always be able to look back on a wonderful, fulfilling life.  
We are who we are.  We won’t grow out of this side of us (and I thank God for that).  Who we wear, and what we wanted to wear, when we were younger is still with us.  It always has been and it always will be. 

Love, Hannah

4 thoughts on “Dressed Like a Daydream

  1. So much of this resonates with me.
    I felt many of those same feelings in school and beyond
    I was never able to fulfill my dreams dressing until the last 10 or so years and I’m a approaching 60
    So it’s difficult to be who we are when we want and need a women in our life but that women just can’t understand this need to be girly
    So we wait and hope and fantasize about the clothes and hope someday we too will be able to dress in all of those lovely clothes


  2. I have from time to time thought about the Renaissance Fair. I always get brought back to earth by the amount of cleavage those dresses show – no way could I pull that off!


  3. Oh I know how you feel at times. Many a day i have wanted come home from work wanting to take off a pair of heels instead of work boots. Would love to work office environment in a nice pencil skirt sheer hose heels a nice satin blouse and a nice blazer. There are days I want to be femme at times because I a lot of times there is another person trapped inside my body.


  4. To begin, the last photo on this post is amazing. Gorgeous beyond words! Ok that out, I too looked at the styles of high school girls and wondered how I’d look in it. Once into the business world…oh the possibilities! We are who we are; proud, happy, and fulfilled on all levels I hope we all acheive!


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