The show Gilmore Girls premiered in 2000 and it remains just as relevant today as it did twenty years ago. The story revolves around Rory's coming-of-age events, such as teen romance, high school drama, and her relationship with her mother. While such themes are timeless, there are certain things that didn't necessarily age that well, such as fashion and increasingly outdated pop culture references.
The residents of Stars Hollow all have a quirky fashion sense, but young Rory never crossed the lines of bad taste. Despite the fact that her outfits obviously belong to another time, fans can still appreciate her style today. She often wore her high school uniform on-screen, so her leisure-time outfits stood out even more than they would otherwise.
Looking Like A Princess
In "Presenting Lorelai Gilmore", Rory makes her debut at the Debutante Ball at Emily's request. This was in the second season of the series, back when Rory was much more agreeable. She has changed profusely throughout the years: she started standing up to herself more, which eventually lead to a big fallout with Lorelai.
When Lorelai was Rory's age, she was supposed to attend the very same event, but she resisted. The event was triggering for her: she saw how much Rory's emotionally unavailable father has changed when he showed up for his daughter for once.
Blue Brings Rory's Eyes Out
One of the many things that the Gilmore girls have in common is their eye color. They both have piercing blue eyes and they both look fantastic in blue. Most of the outfits they wore are outdated by now since they scream early 2000s.
Rory's blue printed dress with an adorable blue cardigan is a fantastic look, but it obviously belongs to a different time. Rory almost always played it safe and elegant, in a cute 00s way.
The Red Polka-Dot Dress Rory Wore To The Dance
In season 3's episode "They Shoot Gilmores, Don't They?", Rory and Lorelai attend the 24-hour dance marathon. It's an episode, filled with teenage love and angst. Sparks between Rory and Jess were flying as they couldn't stop arguing with each other. Dean noticed the passion with which they interacted, leaving him frustrated.
Rory wore a red polka-dot dress to the dance competition. It's too bad that she didn't wear red outfits more often since she looked so radiant in this one. She did, however, wear polka-dot prints on several other occasions.
Rory Looks Best In The Fall
While Rory always stayed true to her comfortable, yet classy looks, her hairstyle changed every season. In season 4, she turned a new page in life since she just ended her tumultuous relationship with Jess and wanted to give Dean another shot.
Everyone's favorite season on Gilmore Girls seems to be the fall since that's when the characters look their best. Rory's dark blue sweater matched her new hairstyle and the colorful trees fabulously. She started to look like a fully-fledged adult rather than a young teenage girl.
Her Cute Purple Dress
When Rory was attending a private high school, she was rarely seen wearing something especially beautiful. Both she and her mother typically dressed to impress when they attended dinner at her grandparents' house. They had to be on their best behavior there.
Rory is an incredibly cute girl and her fashion choices only further emphasized that fact. She never wore anything shocking or controversial. Unlike her mother, she wasn't really a rebellious type.
Looking Preppy At Yale
It wasn't until Rory went to Yale that her personal style started developing independently from her mother's. Lorelai and Rory are very similar in many ways, but not in their fashion sense.
One of the best outfits she wore in her early days at Yale was a plaid mini-skirt, paired with a brown leather jacket that perfectly match her boots. No wonder Logan was so smitten with her: not only was she incredibly bright, but she also looked like a model.
Her Blue Trench Coat
This blue trench coat that Rory wore around the campus is one of her greatest pieces of wardrobe. Unfortunately, we can't say the same about what is going on under that coat. The plaid skirt with huge buttons is unflattering as is her decision to wear a red top under the fabulous blue coat.
Compared to other students on the campus in the background, she looks the most professional of them all.
Rory Looked Mature For Her Age
In season 6, Rory saw Jess again and she wore a truly unique jacket that emphasized how much she has grown since their last encounter. When Jess and Rory first started hanging out, she was regularly wearing her Chilton uniform. Now, she had curly hair and rocked adult looks.
While Rory's style changed, Jess's stayed the same. He was the same denim-loving young man that he has been since his early teenage years. He urged Rory to run away with him and drop out of Yale. While we all secretly wanted their relationship to succeed, Rory followed her head and turned him down.
Her Big Comfy White Sweater
A huge white woolly sweater is arguably the best outfit one could wear in Stars Hollow once the summer is over. Dressed in white, Rory looks even more innocent and angelic than usual.
She wore this outfit in the pilot episode, spending the day with her best friend Lane Kim. Since they grew up together, they remained life-long friends, even though their friendship sometimes felt fake and dishonest.
The Dress She Wore To Meet Logan's Parents
The only thing we loved about Rory spending time with Logan and his family was the outfit that she chose for the occasion. This purple dress personifies Rory's persona: she strives to come across as elegant, serious and grounded.
Her mother, on the other hand, always dressed way more casually and youthfully. When it comes to comparing Rory's fashion style with Lorelai's best and worst outfits, Rory is definitely the more fashion-conscious of the two.