13. The Awkward Hair Clip
Sure, it was the first season and sure, at this point in time Rory was only concerned with books and keeping up with her Mom’s pop culture references — and probably struggling through the early stages of a developing coffee addiction — but sometimes, there just ain’t nothin’ cute about a clip. Sorry, Rory.
12. The Chilton Classic
Rory took all she needed from this super fancy school: A great (but pointless) application to Harvard, an introduction to her future roomie Paris Geller, and a brief encounter with hot Tristan — also known as Chad Michael Murray. She wasn’t there to make a style statement, despite the high importance placed on trivial concerns. Like the length of the uniform hem by her classmates.
11. The Headband
Because what else would one wear whilst reading Sylvia Plath in the town square?
10. The Headband 2.0
Slightly better than the original, the headband 2.0 had an extra touch of sophistication. Totally appropriate for dinner on Friday night.
9. The Pretty Layers
We totally get that Rory was busy with finals, but if she’s trying to say there wasn’t any time for her to visit a salon, we’d say we detect a liar.
8. The Schoolgirl’s Pony
Need to dominate in class, win hearts and still provide Stars Hollow with proof your mother isn’t the only one with top notch banter? You need to have your hair out of your face. Add ribbon for extra cute.
7. The Chanelling-Emily-Gilmore Pony
Rory might not have been our favorite person when she got all DAR-savvy on us, but at least she pulled off the look that matched.
6. The Stylish-But-Mainly-Smart Chop
What works better under a navy cap than some soft feathering around the face? Not much, we’re guessing.
5. The I-Was-Not-Expecting-This Crop
From long and oh-so luscious, Rory went to short and trendy faster than Lorelai can recite the menu at Luke’s. Read: pretty damn fast.
4. The Crop (Minus Newspaper Hat)
Most would argue it works better than the original. Others may disagree. We respect both opinions, because this length was out of the Gilmore World.
3. The Logan Locks
Whether you were Team Logan or Team Anyone But Logan Please, there’s no denying that while the Gilmore name didn’t always fly with the Huntzberger clan, Rory’s hair was definitely up to scratch.
2. The Fringe Benefits
In previous seasons, Rory had dabbled with different bangs. This was the reason behind her very questionable choices of headbands and clips, perhaps? While we will never know the styles Lorelia bestowed on her daughter before Gilmore Girls began, it’s pretty safe to say that Rory must have been pretty relieved to look in the mirror and see this perfect face-framer staring back at her.
While Rory wasn’t always the perfect daughter, student or girlfriend — she came as close as humanly possible. It would be insane to suggest that there could be a single hairstyle that could ever be completely flawless, but, if there was, we’d argue that this is it, right here.