The fast-talking, coffee-loving Gilmore Girls possess so much more than just charm and quick wit. They’re flawlessly beautiful and effortlessly stylish, consistently pushing fashion boundaries through their seven-season run, and then maintaining those fashion standards in the long-awaited follow-up series Gilmore Girls: A Year in the Life.
Undeniably, Lorelai takes more fashion risks than her daughter. While Rory may be inspired by Lorelai’s daring fashion choices, Rory’s style is essentially more simplistic. Her priorities throughout the earlier seasons of the show were on her studies and getting into an Ivy League college, so it's understandable that she didn’t initially spend too much time and attention on her clothing. However, fans would no doubt have noticed how Rory's wardrobe transforms over the years, reflecting changes in both her personal and professional life.
Taking a look back at her style evolution, here are 5 of Rory’s best outfits and 5 of her worst.
BEST: Her Chilton uniform
Rory Gilmore’s Chilton uniform is nothing short of iconic. She attends the prestigious school from Seasons 1 to 3, and viewers are treated to various forms of the uniform throughout those three academic years. Some days, Rory styles it up with just the sweater vest, other days she’s rocking the preppy blazer – often it’s both, sometimes it’s neither. Needless to say, Rory’s ever-changing Chilton uniform really keeps viewers on their toes.
WORST: This ill-fitting floral top
Honestly, it’s not easy to find clothing that Rory Gilmore can’t pull off, but this questionable fashion choice unfortunately falls into that category. The fit of this top is really poor, and there’s just so much happening with the pattern and colors that we’re not really sure where to look. The stripes at the bottom of the top also make Rory look much wider than she is, which is mind-blowing considering what a slim frame she has.
BEST: Her debutante dress
In Season 2’s episode, “Presenting Lorelai Gilmore,” Rory formally comes out to society as a favor to her grandmother Emily. After some initial hesitation, Rory warms to the idea of dressing up, and exhibits this stunning white debutante dress, truly outshining all the other attendees at the debutante ball.
WORST: This underwhelming red shirt dress
Gilmore Girls: A Year In The Life let Rory down in many ways, but few worse than with this unflattering red shirt dress. At the start of the series, it seems like Rory’s career is right on track as a freelance journalist. However, we quickly find out that she’s not exactly thriving in her industry, which is exemplified in this scene where she's having an underwhelming interview at SandeeSays.
We’ll cut her a break though, considering she thought she was actually being offered the job, not being interviewed for it, hence why she may have dressed as such.
On the whole, Rory’s looks in Gilmore Girls: A Year in the Life were hit and miss, but she really hit it out of the park with this look. This chic dress, coat and handbag combination show how much Rory’s style has matured from the original series.
While things may not have been going great in her personal life, this outfit totally distracts from that, portraying a woman who actually has her life together and showing how to "fake it ‘til you make it" with a look.
WORST: The Donna Reed dress
OK, so she doesn’t look terrible, but this outfit has to go in the worst category because of the whole premise of why she’s dressed like this.
In the Season 1 episode, “That Damn Donna Reed,” Rory and Dean argue about the 1950s domestic behavior of Donna Reed. To prove her point, Rory dresses up like Donna to cook a meal for Dean while cat-sitting for Babette. It just all seems like far too much effort to win an argument, and we doubt Rory had any use for this outfit again. We hope.
BEST: This dress from the Stars Hollow Dance Marathon
In arguably one of the best episodes from the entire show, titled, “They Shoot Gilmores, Don’t They?” Lorelai forces Rory to team up with her for the annual 24-hour Stars Hollow dance marathon after her original partner drops out. They, of course, completely steal the show with these incredible looks and also manage to stay this immaculate throughout the 24-hour stint. We couldn’t possibly decide between the two looks, but this is definitely one of Rory’s strongest outfits so far.
WORST: This unflattering pink sweater
It’s a running joke throughout the series that Lorelai and Rory can eat whatever they want and stay slim, and there’s no denying the fact that they really do have INCREDIBLE figures. Which is why it’s so frustrating when Rory chooses to put something like this frumpy, ill-fitting pink sweater on. The placing of the image on the sweater is obviously unflattering, and possibly worst of all, she’s wearing it at Harvard University, of all places!
In the Season 2 episode, “Road Trip To Harvard,” Lorelai and Rory take an unexpected road trip after Lorelai calls off her wedding to Max Medina. They didn’t go on their travels with the intention of visiting Harvard, so Rory could probably be excused for the lack of preparation. However, she can't be forgiven for owning this hideous sweater in the first place.
BEST: Her WWII-themed outfit
In the Season 6 episode, “We've Got Magic to Do,” Rory went for this stunning look at the charity event she organized – a World War II-themed DAR (Daughters of the American Revolution) bash. Her make-up, hair, and outfit is perfection, and it almost distracts from the drama that went down that evening, where Richard (finally) confronts Mitchum Huntzberger for his mistreatment of Rory.
WORST: This frumpy gray sweater
We know Rory’s style in the earlier seasons is quite simplistic, but this gray sweater is dull and boring – totally disconnected from Rory’s charming personality. Yes, it looks comfortable, but with her mother standing there killing it in a simple tee and black leather jacket, we can’t help but feel that Rory sadly missed the mark with this one.