You could be pretty if you tried

I’ve been trying to write this post for two years. It hits something deep, pervasive, and almost too overwhelming to try to write down so I start and stop in fits of anger and sadness.

“You could be pretty if you tried”

The above quote is something that was said to me when I was in 7th grade. The person who said it was an 8th grade and, honestly, she probably doesn’t even remember it because this was probably a normal thing for her to say to someone like me. I never cared much for what I wore growing up. If it was comfortable and covered most of my body – I was set. For most of middle school and high school, I couldn’t afford to spend money on new clothes. Fortunately, I didn’t grow much after 8th grade (I do wish I was a couple of inches taller to make it easier in sports 😉 ). I never struggled too much with what I wore. I shrugged off comments and focused more on figuring out who I was as a person rather than what I looked like.

Looking back on this time, I wanted to be invisible. I had my period very early in 5th grade. I was developing faster than other girls. I didn’t want male attention at all — a very early sign of my queerness. I cut myself when I was 13 very visibly which then brought on even more unwanted attention. Cue me wearing oversized hoodies in 90 degree FL weather nearly every day at school for the rest of middle school and high school. I did not want to be noticed. I did not want to be sexualized. I did not want to be judged. I did not want to be prodded. I did not want suggestions on what to wear. I did not want to be told how to be. I wanted to be left alone.

We talk about lowering the barriers to entry in tech to make our products easier to use. It’s almost as if in my little brain, I wanted to put up a barrier for people to get to know me. If they were superficial and wanting to be my friend because of something silly like what I wore, I didn’t want to be friends with them. Dressing horribly weeded these people out of my life. It also made the people I was close with friends with me for me — not because I was some trendy girl.

As I got older, I thought this would get easier. College came and I still remember the panic of heading to school. I bought all new clothes that were enough me yet “cool” enough that I might pass. I cried when I went on this shopping trip (paid for by my appearance driven grandmother) with my mom. I saw the bill come up for the clothes we were getting that I didn’t even need or want and it made me sick to my stomach. I knew how much that money could do for people who actually needed it. I cried and walked out of the mall in a complete stupor at what I had just done.

The first couple of days of college, I tried so hard to look like those same girls in high school who made those passing comments. It was so damn uncomfortable. Within a week, I was rolling into class in a t-shirt and soccer shorts. For part of college, I was myself. I was surrounded by an athletic community and I fell right into it. I looked around and saw people dressing like me. I walked into a conversation and wasn’t immediately judged for what I was wearing. I never got any comments about what I wore from the rugby community. I am eternally grateful for this as it freed me up mentally and emotionally to focus on understanding/accepting my sexuality. At the time, any comments from fellow ruggers fell more in line with how I dressed and acted that the comments fell under my radar.

Towards the end of college, things changed. I was ramping up for the real world and I started finding myself in a new circle of folks as a result. The comments began rolling in right when I got used to not hearing them:

“You should wear makeup”

“Oh my gosh – your ears aren’t pierced?”

“Just try this dress on – it won’t kill you. Plus you’ll look cute for a change.”

“Put your hair down! It looks so boring up. What a waste.”

“Open up that button at the top of your shirt. You’re always so conservative. There’s nothing wrong with cleavage.”

It’s confusing – Why am I so uncomfortable? Am I uncomfortable with my femininity? Are these people saying these things just trying to help me become more comfortable? What’s wrong with me for just simply not caring? Why do I have to justify myself? Why does it matter what I wear? Should I fight this? If I don’t care what I wear, should I just put the dress on? I honestly don’t think much about what I wear. Nomading has made this even worse as I really only have so many options that I can cram into my backpack. Personally, I love it. It fits my personality and my lifestyle perfectly. For someone with certain expectations of how I should look though, it’s shocking.

I saw “The Mask You Live In” tonight (more like 1.5 years ago at this point – remember I’ve been writing this for 2 years) and it hit me while watching the film that in many ways I was dealing with similar struggles. Constantly hearing that how you look isn’t enough makes you feel like you aren’t enough. Over the last couple of years, I’ve dipped into what so many women experienced for years while I donned my hoodies and plugged my ears.

People critiquing me comes in waves. Early on, I was excused as a tomboy and was lucky enough to go to an elementary school with a strict dress code meaning I could blend. Then middle school hit and wave 1 started. In a strange twist of fate, I was emotionally fucked up enough to harm myself which seemingly actually protected me longer term from some of the damaging things girls learn at this age about appearance. Hiding under my big hoodies was the best thing I could have done as a girl at that age. Under my hoodies, I wore my sports bras and t-shirts comfortable as I could be. Under my hoodies, I wasn’t seen as a sexual object. Under my hoodies, I was neutralized. I forced people to see me as a person.

I was still affected by the rhetoric. I still knew I was rebelling. I still got comments like, “You should put bows in your hair if you’re going to wear it up all the time. Otherwise, people are going to think you’re a lesbian” (said to me by a church staff member in 11th grade). When college came, it came crashing on me how ill-prepared I was for all of these things women my age had been learning and practicing for years! I knew nothing about makeup. I only knew how to put my hair up in a pony tail. I panicked. It felt like coming to work or class unprepared. This is when the crying shopping trip happened.


After college, I dated someone very involved in appearance in every way. I didn’t have a hoodie to hide under at this point. After years of avoiding this criticism of what to wear, I fell straight into it as I fell in love. I wore scarves. I “invested” in new jackets. I dug through the back of my closet at my parent’s home trying to find that one nice pair of shoes my parents bought me that I never wore. I wore them. I wore my hair down even though I hated every second of it. I started wearing my glasses more – I hate wearing glasses. Somehow in the decade + after I got glasses, glasses had moved from an object of ridicule to a fashion accessory. Who knew? I didn’t. In San Francisco, a city where anything goes, I was the most restricted I’ve probably ever been as an adult. I played the part I was asked to play. At times, I fought it and refused to play dress up. Ironically, one of the last acts of that relationship was me buying a leather dress for an event we were going to. Until the very end, I was committed to blending.

When this relationship ended, it took me months to find my old t-shirt wearing self. I laugh now but I was in Seattle with friends after the breakup when we were about to leave the apartment to go to dinner. I was in my classic athletic attire and turned around to change saying, “I can’t leave in this”. My two friends stopped in their tracks horrified. “Anne, what the fuck. Come with us now. You can wear whatever you want with us.” Oh… right. OH RIGHT.

As I’ve come into my queer identity, I’ve noticed a new trend in people telling me what to wear and how to present myself. I am finding I’m not queer looking enough yet I’m not feminine enough. I was with a group of heterosexual women at a bachelorette weekend this past year when my friend, the bride, asked “Would you all think she’s gay?”. They all nervously looked at me obviously confused that I was and afraid my friend was accusing me of something I wasn’t. I passed as straight in that setting albeit still leaning on the tomboy/plain side. If you ask any queer person if I could ever pass as straight, they will laugh in your face. They so obviously see me as queer. If you ask the guys who offer to buy my drinks/walk me home/[insert action], they will very clearly think I’m straight. I can blend on both sides.

I’m finding there’s a problem with this blending. I am told to wear more cut offs and chop off my hair from queer folks. I am being told that I’m denying my queerness by not wanting to. I am being told I’m afraid. I am being told the same by other straight women. I’m afraid of my sexual power so I hide my cleavage. “Embrace it” – both sides scream and yank at me. I don’t want to have anything to do with it. I walk a very thin line on both sides.

Let me provide an example using flannel shirts. For the same bachelorette party I mentioned earlier, I needed a flannel shirt.  <sarcasm> We were all going to put makeup on and wear flannel and have a girls’ night out at country night! WOOHOO <sarcasm>. I don’t wear makeup and I didn’t have a flannel t-shirt. The bride had to snag one for me. When I looked around at everyone putting makeup on wearing their flannel shirt, I busted out laughing. I had been through this exact scenario but with a group of lesbians in college at a house party. Everyone wearing flannel but me in my little, random t-shirt. “How do you not have a flannel shirt?! Are you even gay?” they all gave me shit as they adjusted their cut offs and styled their short haircuts.

I feel just as much pressure to look a certain way as a queer woman as I do as a woman in general. They are different kinds of pressure but the core of it is the same – care about how you look & fit in.

Nowadays, I’ve upgraded from hoodies to actual nice, adult jackets. I have a quick one liner about minimalism when someone expresses outrage that I don’t have [enter item of clothing]. For some reason, minimalism as an excuse is easier for others to swallow than me just not caring. Every woman is bred to care about how they look. Our whole world is designed around it.

Sure – I could be “pretty if I tried” but to what end? Then what? That’s what gets me. I’m pretty then I can… ride off into the sunset? start a business? have a career? get married? WHAT? I don’t care to be pretty. I care about being kind, about being smart, about working hard, about helping others — there’s too much for me to care about for me to care about being pretty.

I will say this – I am lucky. My parents chose a surrogate mother who is the epitome of these absolutely fucked up beauty standards: blonde hair, blue eyes, and pale skin (#,#). I have straight blonde hair and “great skin” (as people like to tell me) without trying. I can not try partially because my baseline is close enough to these stupid beauty standards we have. It’s infuriating for me to think about. It is a privileged infuriation.

There’s a local coffee shop in San Diego that has become my second home. I came in there one day this week ranting and rambling about a book I was reading. One of the awesome baristas shared the book she was reading – “Unspeakable Things” by Laurie Penny:

I came in today to relax and read when the same barista whipped out her copy that she brought from home hoping I’d be coming in today (can you tell I’m a regular there?). I sped through 54 pages of the book absolutely engrossed in every word. I didn’t want to give it back – the book was breaking my heart and building me up all at once. I don’t know where to begin but I imagine this post is going to be one of many rants to come.

These words have always haunted, fascinated, and confused me: “You could be pretty if you tried”. They so perfectly sum up in a tweet like form a complex structure in which so many women live. As if I’m supposed to try. As if being pretty is a worthwhile aim. As if I’m not enough as I am now. I find the words still relevant today and am afraid I will for the rest of my life.



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One response to “You could be pretty if you tried”

  1. There is so much I want to say… this post struck me deeply on so many levels that I don’t think I can possibly tease them all out in one comment. As a bisexual woman, this just touched upon my own experience with physical appearance and identity – lesbians have always told me I “look too straight” to be noticed or desired. I laughed out loud when I read the part about the flannel shirts – this was my life when I was dating women (I’m currently in a long-term relationship with a man, which almost seems less judgmental in a surprising and sad way). In any case, thank you so much for putting a voice to these thoughts and your own experience. Your words and ideas are what make you beautiful; NOT what you wear. Keep doing you, you are awesome. 🙂

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