How I Learned to Stop Worrying and Love Dresses (and lingerie and leggings and…)

The majority of emails I receive ask me “how do I crossdress?”.

The most read feature on my website is “A Beginner’s Guide to Crossdressing”.

The phrase that is most commonly googled to find my website is some variation of someone asking how to become a crossdresser.

By my personal definition of what crossdressing is, crossdressing is probably one of the easiest things in the world.  Put on a pair of panties and you, you gorgeous creature, you are crossdressing.

But I know it’s more complex than that.

Instead of asking how do you crossdress, it’s more helpful to think about what your goals are.  Are you looking to get better at makeup?  Are you looking to learn how to walk in stilettos?  Are you looking for your dress size?  Are you looking to accept yourself?

Each of these goals are different from each other, and I could (and probably already have) written about them.

For some of us, we identify as men who like to wear lingerie.  For others, this is our first step to identifying as bi-gender or gender fluid or as transgender or as a girl.  Clothes can have everything… and nothing to do with one’s gender identity.  When I was younger I used to wonder why I wanted to wear panties and lipstick, but I quickly got over that.

In my opinion, the first step in crossdressing is getting over the thinking that some clothes are for boys and some clothes are for girls.  I know some of us wear certain clothes BECAUSE they are “girl clothes”, but I don’t wear a dress or a bra because I want to BE a girl.  Yes, I want to be a “her” when I am en femme, but I have no desire to transition or live full time.

Although I feel a deep sense of connection and… well, intimacy towards certain clothes, I know that they are just pieces of fabric. A t-shirt with a v-neck is supposed to be for girls but a t-shirt with a scoop neck is for boys?  Ridiculous.  But clothes (and even nail polish) can be a lightening rod for controversy and panic.  After years of going out en femme with very little unpleasant moments and interactions, I have little trepidation when it comes to going (almost) anywhere.  But leaving the house in boy mode wearing leggings or a little eyeliner would terrify me.   Then again, the idea of walking through the mall or downtown en femme used to be unthinkable.

I’ve been wanting to wear (and have been wearing) “girls clothes” for my entire life.  Even now as I type this I am in “boy mode” but wearing my favorite black leggings, a cami, a femme t-shirt, and cardigan.  It’s probably the most comfortable outfit in the world.  Perfect for working at home or doing chores or having a coffee.

Anyone who has worn a nightgown or leggings would tell you how comfortable it is to dress like this.  Yes, I suppose I am crossdressing, but really, I am just wearing clothes.  I don’t genderize clothes.  Or colors.  Or careers.  Or hobbies.  Or bodies.  I wear what I want.  At home, anyway.

If you want to learn how to crossdress, you must first think of what your goals are.  But your first step is getting over the thinking that boys don’t wear ___________.  Wear the leggings, wing that eyeliner, rock those heels.  So much of what we want to do begins with changing our thinking.

They are just clothes.  But at the same time, they are more than clothes.

If you know what I mean.

Love, Hannah


4 thoughts on “How I Learned to Stop Worrying and Love Dresses (and lingerie and leggings and…)

  1. I classify myself as a crossdresser these days. In my youth I had the female face and body – more woman than man. But my puberty messed that up as kicked in very late (29). This changed me body big time. Now my body shape dictates that I will never have the female body I feel I need. My head tells me that I am basically a woman who would prefer to dress that way but when your body structure is more body builder than super model it doesnt work as well. When I was in my 20s no one questioned my gender , which was handy as it was regarded as disgusting in the UK, Out in public I have always been accepted as a woman here and abroad. Been dressing 40 + years but going full time was never an option oncemy body shape altered. For me the key change is nail polish , I have 1″ talons , once my nails are done I am Diana


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