28 Hats I Wore When I Thought I Was Straight, Ranked from Gay to Gayest

28.


Look at this smol gay princess in her sparkling tiara.


27.


Looking totally straight and not at all gay on the ski slopes! Especially in those stupid sunglasses I bought just because I saw a picture of Jennifer Lopez in a magazine wearing a similar pair!


26.


A very sensible Brazil soccer team hat I wore so that cute girls would talk to me about soccer.


25.


How did I get this bucket hat to flip so delicately like that? Gay magic.


24.


Just a beach gal in her beach hat.


23.


Tbh the outfit is gayer than the fancy bonnet, but I think Fancy Bonnet Lesbian is a label I would like to start using for myself.


22.


Not to brag, but this is a custom-made watermelon hat to go with my custom-made watermelon dress. Thanks, grandma!


21.


I went to the club one time during my college years. This photo was taken at the club. I wore this hat to a (straight) club.


20.


This oversized hot pink fleece bucket hat is one of the boldest fashion statements of my youth.


19.


I didn’t know what this kind of hat was called, so I Googled “hat that looks like a hairnet,” and apparently it is called a SNOOD. I wore this “snood” during my hippie phase :/


18.


I took a yellow baseball cap and drew a triangle between two tildes on it with a Sharpie just to really drive home the fact that I was an active tumblr user.


17.


I am sure I am saying something incredibly important here, like “CAROLINE AND ALISA ON THE TELEVISION SHOW ZOOM ARE DEFINITELY GAL PALS.” My sister is clearly having none of it.


16.


A backwards, checkered hat to match my sleeveless checkered tank top (!!!) and denim overalls.


15.


These are technically masks and not hats, but they seemed important to include. It’s like, we get it, you were a nerd.


14.


This is a curling hat that I wore during my first and only curling competition. I know curling isn’t generally stereotyped as a “gay sport,” but that’s because most people do not think about curling in any capacity. I am here to tell you that curling is a gay sport. Spread the word.


13.


This is a collapsible hat purchased in Thailand. It later became a prop in Jenny Bond, a James Bond spoof movie my sister and I made with our Norwegian cousins starring me as Jenny Bond.


12.


Here I am, inexplicably wearing a bandana wrapped around a baseball cap… while doing some lite construction. Nothing gay to see here!


11.


I worked on several political campaigns throughout high school, and here I am knocking on doors for a Virginia gubernatorial primary, sporting my very stylish “canvassing hat.” (Fun fact: A few years later, I was a Teenage Campaign Manager, which is definitely the title of my forthcoming autobiographical Disney Channel series and also a story for another time.)


10.


Oh, you thought you would emerge from this post without an I <3 NY beanie sighting? How foolish of you.


9.


I believe I purchased this hat because one of the Cheetah Girls wore something similar to it?


8.


Does this one even need an explanation?


7.


My mom sewed me a cat-patterned dress with a cat-patterned hat to match. Maybe she really did know I was gay all along.


6.


I thought I looked so cool (and heterosexual!) walking around the streets of New York City in this goofy-ass hat.


5.


At first look, it may appear that I am wearing a cowboy hat in this picture, but I am actually wearing a Rocky Mountain Park Ranger hat, which is somehow even gayer.


4.


Why.


3.


There’s that bandana OVER a hat look again?! WHO DID THIS?


2.


Ah, yes, the natural evolution of Hat #9. The photo on the right looks like it could be the poster for Teenage Campaign Manager.


1.


Mirror, mirror on the wall, what’s the gayest hat of all?

Kayla Kumari Upadhyaya is a Brooklyn-based writer, television critic, and comedian who spends most of her time over-analyzing queer subtext on television, singing "Take Me Or Leave Me" in public places, and assembling cheese platters. She has a cat named after Piper Halliwell from Charmed, and her go-to karaoke song is "Everywhere" by Michelle Branch. Her writing can also be found at The A.V. Club and The Hollywood Reporter, and she wrote the webseries Sidetrack. You can catch her screaming in all-caps about Kalinda Sharma, Jennifer Lopez, and oysters on Twitter and Instagram.

Kayla has written 168 articles for us.

26 Comments

  1. Love it!

    All my hat choices after puberty have been pretty “little old cishet lady”, the kind that makes white old men and Jehova’s witnesses stop in the street and compliment you on your surprising respectability for your age. Mostly because for roughly 10 years after high school I got hooked on not being spat and shouted at by strangers, and tweaked my whole look to achieve optimum kindness.

    Somehow, just a few years before realising how unhappy this made me, this vintage turban snuck into the repertoire. I’m no expert, but I think it’s a fairly queer look. What do you think?

  2. I love this so much, hahaha. I cut all my hair off a while back, which has made me more me. But, it makes me miss hats so much! This precious hair style just can’t succumb to hat hair any longer.

  3. This made me laugh out loud in public.

    I’ve read about snoods in historical fiction but I had no idea that they’re those little hairnet looking hats. Who knew?

  4. Growing up, I didn’t wear many hats, gay or otherwise. But.

    My favorite shirt in high school was a black and blue checked flannel with snaps instead of buttons. It was the most expensive item I bought for myself with my clothing allowance. It was beautifully made and lasted for decades. I still own it.

    I loved it so so much. I wore it everywhere and with everything. I even wore it to church, paired with a white blouse and black wool skirt. Exactly what all the hetero young women were wearing.

    Looking back, it’s kind of amazing that it took me until I was 21 to realize I’m queer.

  5. I, however, own the bi-est hat. It’s a stocking cap with “BI” embroidered big on the front.

    Whoever ordered them for my group at work clearly didn’t think of the other things that the letters B and I could mean.

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