“Why Don’t You Wear Dresses?”

Raise your hand if you’ve been asked this question: “Why don’t you wear dresses?” Yep, that’s a lot of hands. And I’m willing to bet good money that everyone who has been confronted with this strange, obnoxious, unanswerable enigma of a question is perceived as a woman. I’ve been asked this all my life and have always kept quiet about it because I could never quite identify why I despise this question so much. Today though, I want to talk about it, partly because it’s just annoying, but mostly because I think this question often has its roots in some harmful assumptions about gender and self expression, and many times, well-intending askers inadvertently cause a lot of annoyance and discomfort for their unsuspecting victims.

I used to be very confused when people asked this. Having grown up in a house surrounded by five acres of towering trees, squishy swamps and bushy salal, my childhood activities largely consisted of tree climbing, bushwhacking, making forts, terrorizing the local deer population (read: attempting to befriend Bambi), riding my bike through the wooded trails and making twiggy, uncomfortable, but fully functional hammocks out of cedar bows. Naturally, I dressed appropriately for my feral flower child activities so, dresses were never a part of my everyday wardrobe. I often associate them with formal-wear, but more than that, I just never really grew accustomed to the feeling of wearing a dress, so when I go clothes shopping, I tend to gravitate towards pants.

Lately, I have been trying to ascertain the correct answer to “Why don’t you wear dresses?” What does that even mean? Do people think that just because they’ve never seen me wear a dress, I have some kind of moral opposition to it? Truth is, I do wear dresses. I even enjoy wearing dresses sometimes. I just prefer pants usually, and somehow that answer never satisfies the inquirers.

Average Inquirer: What are you talking about? You never wear dresses! I’ve never seen you in one!

Me: Yes, but you’ve only known me for 2 years. And you don’t even see me that often. I do wear dresses, it’s just that I haven’t worn one around you.

A.I: You should wear them more often then, you’d look so pretty!

And you know what? I look bitchin’ in a dress. I feel bitchin’ in a dress. I like the flowyness and the old fashioned vibe and the fact that it excuses me from having to match two pieces of clothing in the morning before I’ve even had my coffee. But there is more to life than looking and yes, even feeling sexy. Sometimes I want to wake up, drag my groggy body to the bathroom mirror, look at my Clearasil dotted face and purple insomniac eye-bags and think, “I’m not sexy today at all. I don’t look it, I don’t feel it, and that doesn’t bother me, because I have things to do and thoughts to have and a life to live and those variables are completely independent of my sexiness.” There’s got to be some kind of healthy level of positive-body-apathy for women to attain. I’m not suggesting that women suddenly become negligent of our health, I’m just saying that this obsession with feeling sexually appealing often feels like nothing more than another polite way of binding women to our bodies.

This question calls a lot of attention to gender expectations. Am I, as a girl, supposed to just naturally feel compelled to wear a certain type of clothing? Why does my explanation of “because I prefer pants, they’re more practical” never satisfy people? It often seems like, as a woman practicality is not a valid reason for my actions. As a woman, I am expected to blindly surrender to whatever beauty standards society sets, regardless of its suitability for my lifestyle. Why is the follow up comment always about how pretty I’d look in a dress, and why is it assumed that beauty should be my motivation for me to wear one? If I wear a dress, it may be because it makes me feel attractive, but more likely it’s because it’s hot outside, or I’m attending a formal event, or I’m out of clean pants. Might I also add that this question reinforces the primitive and damaging concept of gendered clothing, something that I believe to be counterproductive in terms of social progress, as well as absolutely preposterous (save for the reasonable sizing variations that arise as a result of anatomical differences). Not to mention, unless they have explicitly asked you, it’s safe to assume that most people are not particularly interested in hearing your evaluation of their expression and style.

More than anything, please consider this: If I like what I’m wearing, kindly let me wear it in peace. This question is uncomfortable for me, because I usually don’t think I’m weird (at least, no weirder than the next person), yet I am forced to question that and wonder if there’s something wrong with me, every time someone asks this. “Why don’t you wear dresses?” may be asked with innocent intentions, but it perpetuates the same benighted stereotypes and societal expectations that humans have been working decades to annihilate, and I hope to see less of this dreadful inquiry in the future.


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