It was the early 2000s, I was 11 and living at my grandmother’s house in Missouri for the summer. The rubber bands on my braces were a mildewy shade of purple, and I had just developed my first addiction: drag and drop dress-up games. Initially looking to dodge the muggy St. Louis summer I would hole up in my grandmother’s computer room, an obscene spatial luxury for someone who grew up in a converted one bedroom in New York. The computer room was also the gym, and also connected to the basement via a laundry chute that I would shriek into just for fun. (It was St. Louis, there wasn’t that much to do.) These games—which for all I knew at the time made up the entirety of the internet—had a very simple premise. There, on the screen, was a semi-nude doll that you could both customize and, you guessed it, dress up. Often these flash games had themes: you could clothe an off-brand version of a Disney Princess, or Miss Americana, or a fairy. I was a tween video game junkie.
These games were a free space for the mind to wander without judgement or approval from others. They had no plot, no competition, no tête-à-tête with other fans, just endless options to toggle between. You didn’t have to defend your personal style—or even have one. There were no stakes. It was all the wonder of playing with your favorite doll without the annoyance of losing a single Barbie shoe, or realizing that their hair, once cut, would never grow back.
It was also a way to maintain childhood play while transitioning into being a teen. By that age my dolls were shoved in a box under my bed because playing with Barbies was for babies, but there I was still playing with dolls, just this time putting them in cute miniskirts. My hobbies were writing in my diary, spending hours looking at clothes online, and daydreaming. What would I be like when I was older? I would wonder, somehow winded from sitting at the computer clicking through various hairstyles, what would I wear when I had more than $100 in withheld bat mitzvah money (money to this day I have yet to see). What would I be like?
For the current crop of Gen-Z fashion writers and creators, now in their mid-twenties, these games were a formative early experience with the internet’s capability to expand what fashion can be. Fashion writer Alexandra Hildreth didn’t even know she wanted to work in fashion until she was almost 20, but there were always signs. “I remember playing games like My Scene on the family desktop when the internet was still fabulously populated by single-interest websites and forums that let you dig into your coming-of-age aesthetic obsessions, and edit your digital doll’s fall coat collection,” she says. “It was all so intensely curatorial but personal, how could that not lead to fashion?”
Creator Clara Perlmutter who goes by @tinyjewishgirl on TikTok and Instagram echoed the sentiment, telling me how the early aughts games helped her experiment with fashion, “I was really into the games on girlsgogames, addictinggames, Stardoll, and i-dressup. My childhood in the early 2000s was a great time for online. I looked up to Britney Spears and Paris Hilton, style-wise, but I was a child so it wasn’t like I could dress like them,” she says. “Dress-up games were kind of like wish fulfillment for me. It was easiest for me to experiment online with simulated fashion when I was kid because my town was small and insular and people were judgmental. But honestly, I stopped caring what people thought at a young age and have been exercising my free will with fashion ever since. And now my job is playing dress-up for a living!”
Those 2000s flash games gave way to things like Roblox’s Dress to Impress, a user-designed competition dress-up game created for the gaming platform Roblox, but there are still plenty of websites where you can dress dolls up the “old fashioned” way. On azealeasdolls.com you can put fun clothes on various people real and imaginary: like Kate Middleton, Thumbelina, Epic Angel and also someone called Natural Girl, who just like the girl reading this, is naturally beautiful. I decided to play around and see if these games held up.
Ultimately, after giving Natural Girl a nasty bob and clicking around the clothing options, I found it mindblowingly, annoyingly, perversely boring. Then I spent the next two hours scrolling through back pages of The RealReal looking for the perfect bag until my contacts started to dry out. If my 11-year-old self could see me now…I’d be exactly the same.
