If It Makes You Happy

“If it makes you happy, it can’t be that bad”

-Sheryl Crow

For me, that feeling never goes away.

The happiness of buying new lingerie, the feel of a zipper sliding up on a cute dress, the power rush of the first steps taken in my stilettos.

These feelings are connected to memories of the first time I entered this beautiful world.  It cannot be described, only experienced.  It’s not unusual for us for feel to a little confusion about all this as we realize that this feels right, that this is something that is a part of us.

I have stopped trying to understand this part of me.  I have stopped trying to determine why I am who I am.  To me, this part of me is simply that.  It’s a part of me.  Literally.   I can’t explain why this part of me makes me happy, it just does.  I can’t explain why this makes you happy, either.  To me, it’s no different than the other things in your life that create joy… whether it is a certain food, a song, or a season.  You just love it and that’s all that matters.

We feel the joy, the confusion.  We also feel the shame, the guilt, and the embarrassment.  But why?

I think some of this comes from being taught that anything feminine is associated with inferiority or weakness. We are told to man up, boys are taunted for throwing like a girl, and that men don’t cry.  These comments are meant to embarrass us.  To shame us.  To humiliate us when we express emotion.  Girls cry, girls wear dresses.  Men are taught it’s embarrassing to be associated with anything feminine, whether it is an emotion or a piece of clothing.

Is it any wonder we felt ashamed or embarrassed when we dressed?

Our feelings about ourselves and others are sometimes influenced about what we are taught and exposed to.  Some of us feel we are too tall to “pass”.  Some of us feel our hands are too big to be feminine.  Some of us feel we are too masculine to be beautiful.  In a way, these perspectives are a result of us being told what a woman “should” look like.  A woman needs to be a certain dress or shoe size, a woman needs to be a certain height or weight, a woman must have a certain face shape….

When we don’t fit these arbitrary and subjective standards, we feel that we can’t be beautiful, we can’t be feminine, we can’t present as the gender we identify as.  But there are no standards we must fit.  There are no standards a woman, cis or trans, must fit.  No one is too tall to be feminine, for example.  Once I realized this, I completely stopped worrying about “passing” and meeting someone else’s expectations of what I needed to look like.  I never looked back.

I can’t recall ever being ashamed about wanting to, or wearing panties or makeup or anything else that is considered feminine.  I was raised by a single mom for most of my childhood and I have two strong and independent sisters.  In my world, women were leaders.  People to emulate.  I was used to being around girls, and I was friends with girls in grade school at an age when that wasn’t normal.

Eventually I got tired of being called a sissy for being friends with girls and started to hang out with the guys instead.  Grade school is tough, and it’s sad how strong gender roles and expectations are enforced even today.

But this side of you is nothing to be ashamed of… unless you think it’s shameful to do anything that is commonly considered feminine.  Perhaps Iggy Pop said it best when he stated  “I’m not ashamed to dress “like a woman” because I don’t think it’s shameful to be a woman.”  I couldn’t have said it better myself.

Years ago I had a coworker who stated he just didn’t “get” people who were transgender.  As he spoke, he said he sort of understood why women wanted to be men, but didn’t see why any man wanted to be a woman.  “It’s a demotion”, he said with a laugh.  I wish I had had the courage to say something at that time.

This perspective is a perfect example of someone who thinks it’s shameful to be a woman.  I don’t think it’s shameful, and I doubt you think so either.

Some of us feel guilt when we dress.  We are going against arbitrary gender roles that we were taught growing up.  Boys do this, girls do that.  Why?  Well….  no one really knows but it’s often explained that these rules are in place because that’s the way it’s always been.  Well, perhaps not always.

Some of us were told that God made us a certain way and we need to remain that way.  If God made you a boy, then you must be a boy.  Doing anything that isn’t “for boys” goes against God’s plan.  As someone who was raised Catholic I can certainly attest to being told to live a certain way because that’s what God wants, but I seriously doubted God cared about what color underwear I wore.

You might feel guilty for keeping this side of you a secret.  We are used to keeping this side of us to ourselves and we likely have gotten quite good at little white lies and concealing things.  Telling a coworker that I had a boring weekend when I really spent Saturday getting a makeover and going shoe shopping is technically a lie, but it’s a lie I can live with.  Lying to our significant others about this side of us is a different story.  This will likely trigger deep feelings of guilt.  Some of us can live with the guilt, some can’t.

I know that this side of us is complicated.  I know that we want to know why we dress, why this makes us happy, what this means.  I know this side of us unleashes countless different feelings from fear to happiness to confusion to excitement to calmness to anxiety.  I know this.  You know this too.  We are told and taught so many things about gender and gender roles from a very young age.  So many things in this world are categorized by gender, whether it is shaving cream, sports, or colors.


These things reinforce any negative feelings we may have about our own gender identity.  We want to paint our nails but boys don’t paint their nails.  We want to wear a nightgown but those are for girls.  We want to be friends with girls but that’s gay. 

If we are to accept and embrace this side of us then we must stop listening to what the world says we must be.

We must listen to our hearts.

We must be who we are.

Love, Hannah




6 thoughts on “If It Makes You Happy

  1. This post is so powerful in its simplicity, if only it were that simple in reality. Being who we are is not a single step across the male-female chasm. Someone else referred to this as a bridge between all male and all female, with varying degrees along the span. Some people stay in one place on the bridge, while others move back and forth between the sides. The journey is difficult yet ultimately rewarding.


  2. Hannah, Thank you so much for this. There is such truth in what you say. It took me (and I’m sure others) much too long to realize we should not be ashamed of who we are, or what we look like. When we consider how many cis-females have less than “perfect” (don’t you just hate that word?) figures, or faces, or voices, we realize that we are part of that spectrum. Some of us may be blessed with less broad shoulders, or light beards, or smaller hands, but even if not, there are ways we can dress to minimize what we perceive as “imperfections”. After all, isn’t that what other women do?


  3. Thank you Hannah for this wonderful post. I’ve had some conflicting feelings about this lately and it really has been tough to sort out. Actually when I was younger I kind of looked at men who dressed in public as weird, even though I’ve worn pantyhose in secret since I was a kid. I don’t feel the same now but I have a strong fear of being found out. It’s something that no one but myself can figure out but it’s nice to read a post like this. So once again I just want to thank you for sharing.


  4. I am beyond done asking myself WHY I like to wear feminine clothing and present myself in public. I have shifted to “Why not?”. I might as well ask “why do I like sushi since I’m not Japanese?” Or “why do I like theatre, art museums and the symphony while most men my age love following pro sports?” As I always say, some women love dresses, some hate ‘em, and most will wear one if the circumstances warrant it. Why shouldn’t there be just as much variety amongst men in the feelings around dresses.


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