Look at this smol gay princess in her sparkling tiara.
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!
A very sensible Brazil soccer team hat I wore so that cute girls would talk to me about soccer.
How did I get this bucket hat to flip so delicately like that? Gay magic.
Just a beach gal in her beach hat.
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.
Not to brag, but this is a custom-made watermelon hat to go with my custom-made watermelon dress. Thanks, grandma!
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.
This oversized hot pink fleece bucket hat is one of the boldest fashion statements of my youth.
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 :/
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.
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.
A backwards, checkered hat to match my sleeveless checkered tank top (!!!) and denim overalls.
These are technically masks and not hats, but they seemed important to include. It’s like, we get it, you were a nerd.
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.
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.
Here I am, inexplicably wearing a bandana wrapped around a baseball cap… while doing some lite construction. Nothing gay to see here!
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.)
Oh, you thought you would emerge from this post without an I <3 NY beanie sighting? How foolish of you.
I believe I purchased this hat because one of the Cheetah Girls wore something similar to it?
Does this one even need an explanation?
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.
I thought I looked so cool (and heterosexual!) walking around the streets of New York City in this goofy-ass hat.
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.
There’s that bandana OVER a hat look again?! WHO DID THIS?
Ah, yes, the natural evolution of Hat #9. The photo on the right looks like it could be the poster for Teenage Campaign Manager.
Mirror, mirror on the wall, what’s the gayest hat of all?