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Midwest Princess
posted December 15, 2025
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I think back to the mid-2000s, when I was starting sixth grade.
In elementary school, I was content wearing Limited Too and Old Navy,
but in middle school, that wouldn’t fly. It was immature. Pedestrian.
The “popular” girls woke up early in the morning to straighten and style
their hair. I wondered if they planned out their outfits and set them
aside the night before, because they always seemed so impeccably
coordinated.
Obviously, my main goal in life was to also be “popular,” or at least not seen as such a loser. Part of the mystique, I realized, was that most of the girls had older sisters. Older sisters that listened went to red cup parties and had boyfriends. Who already bought a bunch of cute clothes to bestow upon their siblings. It was one thing I always longed for and could never have.
The Midwest Princess (yes I borrowed it from Chappell Roan who is otherwise unrelated to this) grew up in a tastefully modern home or garish McMansion. Her parents collect art, as did her grandparents. Let’s be real here, by the way. Her dad is kind of an awkward neb with a really good job, and her mom is turbo-hot, funny, and probably has some plastic surgery. She’s very “cool mom” who carries a Chanel bag and for some reason insists on driving an SUV. Mom probably gave the whole “you can drink in the house as long as you’re safe and don’t go driving and don’t tell your parents” type spiel to all of her friends. I mean, the estate is sprawling, so it’s pretty hard to not party in it.
But this version of the Midwest Princess has since grown up, a little bit. She’s in college now, pledged for a sorority and studying Communications so she can live out her dream of working in PR. You can find her on campus in her Hard Tail foldover dance pants, a Michael Stars thermal tee, and either Uggs or Birkenstock clogs depending on the season. There’s usually some kind of North Face outerwear thrown on top, too. Her taste may not be innovative or even very interesting, but you can guarantee she will always match her friends.
It’s a joke, right? Totally a joke!!!!
I gave up on trying to emulate her by the time middle school was over. As I’ve detailed before, the urge to go more decidedly alt kind of clashed with that whole vibe. But I still went to Camp Tamarack, so I wasn’t impervious (was pervious?) to their influence. I didn’t fit the mold, though, because I was just too fucking awkward. Maybe that bred a little bit of resentment. I wasn’t dancerly, or beautiful-haired, or even slightly charming. My parents didn’t have the “right” jobs. And I’d come to find out that even my friends who did have the “right” background didn’t fit in if they weren’t perfectly petite and glamorous or whatever. I still lusted after designer jeans and North Faces and UGGs because I wanted to prove something. Like maybe if I dressed differently they’d see me as one of them.
I gave up on trying to emulate her by the time middle school was over. Despite buying nice clothes at the discount store, I never passed muster. Maybe that bred a little bit of resentment. I wasn’t dancerly, or beautiful-haired, or even slightly charming, so I turned it into a fantasy I rejected and mocked. It was easier to pretend I was above it, even though assimilation would have felt better. As I’ve detailed before, the urge to go more decidedly alt kind of clashed with that whole vibe.
Ironically, I remember the day I came back to school from my middle school after obtaining a Livestrong bracelet and a sweater from Hollister. I had fully put my Old Navy past behind me. And I was sort of surprised that nobody seemed to care or notice. I went on throughout high school acting like for some reason I was better than the “generic” popular girls even though I secretly wanted to be just like them, and get invited to parties and wear Hardtails and be “hot.” Here are some items in particular I always wanted and never got.
Obviously, my main goal in life was to also be “popular,” or at least not seen as such a loser. Part of the mystique, I realized, was that most of the girls had older sisters. Older sisters that listened went to red cup parties and had boyfriends. Who already bought a bunch of cute clothes to bestow upon their siblings. It was one thing I always longed for and could never have.
The Midwest Princess (yes I borrowed it from Chappell Roan who is otherwise unrelated to this) grew up in a tastefully modern home or garish McMansion. Her parents collect art, as did her grandparents. Let’s be real here, by the way. Her dad is kind of an awkward neb with a really good job, and her mom is turbo-hot, funny, and probably has some plastic surgery. She’s very “cool mom” who carries a Chanel bag and for some reason insists on driving an SUV. Mom probably gave the whole “you can drink in the house as long as you’re safe and don’t go driving and don’t tell your parents” type spiel to all of her friends. I mean, the estate is sprawling, so it’s pretty hard to not party in it.
But this version of the Midwest Princess has since grown up, a little bit. She’s in college now, pledged for a sorority and studying Communications so she can live out her dream of working in PR. You can find her on campus in her Hard Tail foldover dance pants, a Michael Stars thermal tee, and either Uggs or Birkenstock clogs depending on the season. There’s usually some kind of North Face outerwear thrown on top, too. Her taste may not be innovative or even very interesting, but you can guarantee she will always match her friends.
I gave up on trying to emulate her by the time middle school was over. As I’ve detailed before, the urge to go more decidedly alt kind of clashed with that whole vibe. But I still went to Camp Tamarack, so I wasn’t impervious (was pervious?) to their influence. I didn’t fit the mold, though, because I was just too fucking awkward. Maybe that bred a little bit of resentment. I wasn’t dancerly, or beautiful-haired, or even slightly charming. My parents didn’t have the “right” jobs. And I’d come to find out that even my friends who did have the “right” background didn’t fit in if they weren’t perfectly petite and glamorous or whatever. I still lusted after designer jeans and North Faces and UGGs because I wanted to prove something. Like maybe if I dressed differently they’d see me as one of them.
I gave up on trying to emulate her by the time middle school was over. Despite buying nice clothes at the discount store, I never passed muster. Maybe that bred a little bit of resentment. I wasn’t dancerly, or beautiful-haired, or even slightly charming, so I turned it into a fantasy I rejected and mocked. It was easier to pretend I was above it, even though assimilation would have felt better. As I’ve detailed before, the urge to go more decidedly alt kind of clashed with that whole vibe.
Muses: LC and Kristen In Laguna Beach, Rachel Bilson, Natalie Portman
Ironically, I remember the day I came back to school from my middle school after obtaining a Livestrong bracelet and a sweater from Hollister. I had fully put my Old Navy past behind me. And I was sort of surprised that nobody seemed to care or notice. I went on throughout high school acting like for some reason I was better than the “generic” popular girls even though I secretly wanted to be just like them, and get invited to parties and wear Hardtails and be “hot.” Here are some items in particular I always wanted and never got.
I gave up on having the innate put-together-ness that the Midwest
Princess displays. She’s type A, organized, athletic, bubbly. The main
things we have in common are that we’re Jewish and like wearing sweats.
And sure, I still feel jealousy sometimes towards Girls Who Have
Everything, but I was never truly cut out for the princess lifestyle
anyway. Happy hanukkah, everyone!