I was twelve years old when a loudmouthed classmate told me I threw a ball “like a boy”.
Everyone laughed as I stood paralysed in shame.
I took it as the insult it was intended to be and cried so hard that night I looked like Sylvester Stallone at the end of Rocky 4 (as a Tomboy, I also gravitated to more “manly” movies).
I felt like the ugliest person ever and also the loneliest.
As the 40-year-old lady that I am today, a regular gym-goer, I love to be complimented for my athletic ability; it’s something I take pride in, and that ball-throwing comment would be met with a genuine “thank you” from this more rounded, confident woman that I have worked on becoming today.
I want to go back in a time machine and take that teary little tomboy by the hand and tell her it’s going to be ok; there will be a future where she is accepted for who she is.
Then we’d probably go and climb some trees together and jump in dirty puddles.
That said, she had to learn the hard way, and that’s usually the best way to learn. Thankfully, I think things have changed for the best, and it will be easier to be a tomboy/masculine woman or whatever new label will be created for women of my ilk.
Here’s my take on the timeline from ‘tomboy shame’ to the hottest aesthetic of our era.
The 1990s-2000s: Tomboy as Outlier
Think Drew Barrymore in baggy cargo pants, young Angelina Jolie with a buzzcut and wallet chain, or Pink rocking a heavily hairsprayed hawk at the VMAs.
It was so cool to witness, but passive-aggressive comments like “They will grow out of it” echoed around and haunted the minds of anyone who feels different but wants to be accepted.
Society tolerated it, but with a hint of suspicion. Get it out of your system, Tomboys. It’s cute you’re expressing yourself (condescending head pat), but don’t forget to leave this behind for womanhood when you’ve grown up.
The Late 2010s: The Great Feminization
Just when you thought all of the peer pressure from magazines might ease up… along came a thing called Instagram.
Contouring tutorials were the norm, long mermaid hair down to your bum was back “in”, and bodycon dresses with how-to-do-your-makeup “the right way” became the default setting.
The tomboys were in trouble.
Suddenly looking “like a girl” wasn’t just expected; it was monetized. Also, users got drunk on dopamine hits every time they received a “like” for their uploads.
It was like high school on steroids.
Awful. Any woman still in a hoodie and sneakers felt pressure to explain herself.
2020-2021: The Pandemic Reset
Although it was a testing time for many, it did shift people’s priorities from aesthetics to comfort.
Sweatpants became socially acceptable. Bras became optional. We all lived in oversized tees for eighteen months and realised… we kind of liked it.
I had to fight off the smug “told you so” in exchange for excitement that the tide was finally turning.
Comfort crept in and refused to leave.
2022-2023: The Runways Catch-up
The Row showed shoulder-padded blazers the size of small tents. Saint Laurent sent models down the runway in men’s neckties and nothing else.
TikTok sounds labelled “masc” racked up billions of views. What started as pandemic laziness suddenly had a couture price tag.
The tomboys tried not to judge themselves too harshly as they let out a girly scream!
2024-2025: Full Mainstream Takeover
Chappell Roan accepts a VMA in a thrifted suit. Straight influencers post “boyfriend wardrobe” hauls. Boss ladies wear oversized Oxfords to the office with no apologies.
The aesthetic that once got kids bullied in playgrounds is now the default setting for half of Gen Z and a growing chunk of millennials.
So, why did it stick this time? How did it become such a hardline à la mode in mainstream culture after being rejected as “just a phase” so many times?
A perfect storm: Gen Z’s rejection of rigid gender roles, therapy-speak normalising comfort over conformity and just exhaustion. I believe many women got tired of contorting.
For further proof of my theory, read our recent write-up: 6 Androgynous Female Celebs With Unapologetic Masculine Energy
On a final note, the intention of this post is to celebrate the rise of the tomboy, not to bash women who dress traditionally feminine (I’d struggle to have any friends in the Elizabeth Street office if I did that!)
I have always dreamed of a day when women of all shapes, sizes, and fashion preferences own their own look and don’t judge others who choose a different path.
Thankfully, I feel like that day is not too far away.