A Love Letter To Rory Gilmore’s School Style: The Only True-To-Form Uniform On TV

When I think back to my private school days in the suburbs of Chicago, it isn’t the assignments or even my teachers that I remember so much as my uniform: a red-and-navy check jumper that was only slightly more exciting than the pieces I was authorised to wear with it. Five days a week, for six long years, I wore the same outfit with either ballet flats or penny loafers — only black or navy — and a polo or Oxford-style shirt. Even my stockings — black, navy, or white knee socks or tights — were not of my choosing. 

In sixth grade, I transferred to public school, shedding my uniform in the process and eventually making a career out of dressing for myself.

The only source of solace I had throughout my elementary school years, though, came in the form of Rory Gilmore, a fellow uniform-wearer however fictitious. The youngest Gilmore Girl wore a real school uniform, like I did, as opposed to the bespoke versions spotted on the Blair Waldorfs and Serena van der Woodsens of New York City’s upper crust. In my busted-up ballet flats, I couldn’t relate to the sorts of uniforms worn by the televised student body, which often included colourful statement handbags and tights, as well as designer belts, padded headbands, and layered-on jewellery. Hell, I wasn’t even allowed to wear nail polish (or say hell), let alone insert a pussy-bow blouse in place of my polo. 

Rory’s Chilton uniform was slightly different, enough to offer me a sense of hope. By my count, the 2003 valedictorian had a total of eight top options throughout her three illustrious years at the East Coast establishment, including one button-down shirt, two vests — one navy and one grey — three jumpers— a navy and a grey cardigan and a navy pullover — a blazer, and a peacoat. Though six more than I had, the restrictive colour palette and lack of eye-catching accessories was in sync with the constraints of my school ensemble. On the bottom, she always wore the same blue plaid skirt, which, apart from colour, was a near-exact replica of the style I would have worn had I remained at my private school past the fifth grade. (In the sixth grade, our plaid jumpers were replaced with equally plaid skirts.) Though her black-and-white Oxford shoes would have likely led to a citation in my day, they were still a far cry from Serena’s Stuart Weitzman thigh-highs. 

Which is not to say that I didn’t enjoy the “uniforms” (can we really refer to them thus?) featured on Gossip Girl. In fact, I loved them. As a longtime fan of both the books and the original TV series, I often daydreamed about wearing a loose tie with an untucked button-down shirt. I thought long and hard about carrying my books in a leather shoulder bag as opposed to a dweeby backpack and accessorising with jewel-tone tights and earrings that weren’t simple gold balls (the only kind we were allowed to wear). Despite being permitted to wear whatever I wanted (within reason — my affinity for short shorts was denied by both my parents and the administration) in high school, I often found myself dressing with Serena and Blair in mind, switching off between the boho and prep valances. I had a lot of missed opportunities to make up for, and wasn’t ready for Rory's more understated sense of style.

But during those years when I didn’t have a choice in how I dressed, back when I had no choice but to relinquish any style autonomy despite my growing interest in fashion, fantasising about clothes that were off-limits felt like a waste of time. Instead, it was Rory’s finite sartorial options that kept me zipping up my jumper and slipping on my loafers every morning. Her rotating selection of mundane cardigans and blazers furnished me with an odd sense of solace. I wasn’t in this alone.

When I do my annual autumn Gilmore Girls rewatch, I’m comforted, not only by Luke’s flannels and Lorelai’s chaotic yet stylish selection of ‘90s graphic tees and zip-ups, but by Rory’s Chilton uniform, which to this day, remains one of the only true-to-form liveries on TV.