Rory's Outfits On 'Gilmore Girls' Are Bad — And That's Why I Love Them

It's time to revisit her questionable fashion debut.

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Gilmore Girls is my comfort show. I re-watch the series from start to finish every year — and that's not counting the random rerun episodes that suck me in when there's nothing else on TV. Like most fanatics, I enjoy the show's quick-wit, fast-talking, Milo Ventimiglia cameos, and the all-too-appropriate pop culture references, seamlessly written into casual conversation.

What I don't idolize, however, are the costumes, or at least not in the same way I do Gossip Girl or Bridgerton. And, there's a reason for that.

Don't get me wrong: The cool-mom aesthetic Lorelai (Lauren Graham) has going on can be fun and quirky, dripping with early 2000s trends I'll forever be nostalgic for (blue eyeshadow, anyone?). But, it can also be wildly eccentric and chaotic — two adjectives I can assure you no one would ever use to define my clothing taste. As for Rory (Alexis Bledel), she's rarely seen wearing anything but a Chilton uniform for three out of the seven seasons the show ran. And, thank goodness for that, because prior to those sweater vests and pleated skirts, Rory commits a fashion faux pas that will forever trigger flashbacks to my own fashion don'ts in high school.

In the pilot episode, after Carole King's angel voice leads us into suburban Connecticut, Rory visits her mom at the Independence Inn. She's wearing a cream colored, oversized, fisherman's knit sweater, black pants, and a choker necklace that looks like it was made of rope. This is, essentially, our first proper introduction to the teen and her style. In my opinion, it's not a great first impression, but it's an impression nonetheless, because in that moment, Rory Gilmore is me during my first years of high school: Awkward, dressing only for comfort, with no idea what her style is.

Sweater Outfits from TV and Movie History That Are Still So Freakin' Good

Even Lorelai, who makes countless idiosyncratic outfit choices over the course of the show (i.e. the time she dropped Rory off on her first day of private school wearing cowboy boots, denim shorts, and a pink tie-dye T-shirt), questions her daughter's getup. "What's with the mumu?" she asks in reference to the shapeless garment. My thoughts, exactly, Lor. My thoughts exactly.

Granted, Rory isn't the type of person who's overly concerned with clothes. She's a bookworm and a scholar who even poses the question, "Who cares if I'm pretty if I fail my finals?" Her ambitions come first — a personality trait that's highly respectable. So, from a character standpoint, a comfortable outfit that's practical for the season (fall) makes sense for Rory. Plus, I imagine that extra-large sweater served as an emotional comfort for the character, given the fact that her Stars Hollow classmates aren't exactly kind to her.

But to be clear, Rory's choice in chunky sweaters isn't the real issue I have with this outfit. It's how the cozy knit was (re: wasn't) styled that still has me perplexed. For reference, this is the year 2000, when the top fashion icons were popstars like Britney Spears and old school Jennifer Lopez. It wasn't unheard of to work statement hats or animal print into your look. Sure, many fashion choices from that time period are now considered questionable at best, but they were typically over-the-top and more intentional. Heck, even Rory's best friend, Lane Kim (Keiko Agena), knew a thing or two about what was 'in' at time, getting creative with layering before class (a trend that's actually come back around in 2021).

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Still, I do understand where Rory's coming from. No matter how many times my sister offered me fashion advice when I was a teenager, I wasn't interested in taking it, either. I wore what was comfortable, and that was that. I even wore a very similar outfit to Rory's once, except it was an overly oversized sweatshirt that swallowed my entire body. I also received feedback that was similar to Lorelai's comment, but mine came from my best friend. "What are you wearing?!" she asked. I still don't have a good answer. Quite frankly, neither did Rory, who dismissed her mother's prodding altogether.

To this day, I can't help but imagine what a pair of leather pants and heeled booties could have done for Rory's small-screen debut. Or, at the very least, an accessory that didn't look like it was made in art class, like a daintier, chain necklace or pretty scarf. At the same time, I guess Rory's lack of concern for fashion is part of her character's charm (the very little that she has, but that's a whole other article). She's meant to portray a real teenage girl who's still figuring out what it means to have a personal style. Her bad fashion choices are what makes her relatable, and I guess that's part of the reason why I have, and will continue to keep watching.

Sometimes, outfits from movies and TV shows stay on our mind long after we've stopped watching. Made a Scene celebrates specific on-screen looks and explores why they're (still) worth obsessing over.

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