- “Gilmore Girls” premiered 20 years ago on The WB, but Rory Gilmore’s style is still iconic.
- Her wardrobe didn’t scream high fashion, but her casual ensembles were totally in style when the show was airing in the early 2000s.
- The character also completely transformed on the few occasions where she had to don formal wear for school dances, cotillions, and weddings.
- Visit Insider’s homepage for more stories.
Fashion might not be the first thing that comes to mind when you think of Rory from “Gilmore Girls.” Instead, you probably think about school, books, and, of course, coffee.
Although Rory never focused much on fashion, she did wear some incredibly trendy signature outfits. She stuck to the basics and kept things simple, but as she grew up, her wardrobe grew with her.
Read on for some of Rory Gilmore’s most iconic looks.
She spread major fall vibes with her giant cosy sweater.
Rory was the epitome of fall in her cosy knits. This gigantic cable-knit sweater that she wore to school looks ridiculously comfortable.
No list would be complete without Rory’s iconic Chilton uniform.
When she transfers to Chilton at the beginning of the series, Rory introduces a school uniform to her wardrobe. Although we see her wearing sweaters and vests throughout her time at the school, this blazer look is one of the best.
She went all out trying to impress her grandpa on a golf outing.
It’s hard to forget the first time the character hung out with her grandpa.
Being Rory, she went all out to impress him with a sophisticated golfing look – which was rather plain until her grandmother insisted on adding the multicoloured hat.
Lorelai made her a gorgeous off-the-shoulder dress for her school dance.
This handmade gown totally fit the mood for the Chilton dance and the delicate flowers in her hair only added to the look.
She looked like a princess at her cotillion.
Attending the event might have been a favour to her grandparents, but Rory completely looked the part in this ballgown. It was rare to see her in formal wear, but she really knew how to pull it off.
Rory was the image of Juliet in this themed gown.
Although it was a costume, not a regular item in her wardrobe, Rory definitely looked like she fit the part of Juliet for the school play in this Elizabethan gown and headpiece.
She danced in style in this red polka-dot dress.
So many things happened during this episode: Rory and Lorelai almost won the Stars Hollow dance competition, Rory tried to make Jess’ girlfriend jealous, and she got dumped for the first time by Dean.
But, through it all, she wore this vintage-inspired red polka-dot dress.
For Thanksgiving, she wore this beautiful red coat and looked way more sophisticated than a high-school student.
Although Rory’s high-school wardrobe was pretty much on-point for what a typical early-2000s teen would wear, this red coat definitely made her look sophisticated for her a Lorelai’s many Thanksgiving meals.
She looked mature when she visited Stars Hollow from Yale.
Rory’s style definitely shifted over the course of the show, especially when she went to college.
When she returned to Stars Hollow for a visit during her freshman year, she looked very mature with her new bob and grey turtleneck sweater.
She wore another iconic costume during the Festival of Living Art.
For Stars Hollow’s Festival of Living Art, Rory portrayed the famous painting “Portrait of a Young Girl Named Antea.”
She wore this gorgeous blue gown when she captured Logan’s heart.
This powder-blue gown that Logan purchased for Rory is breathtaking. Although the outfit isn’t something Rory would typically wear, it’s still one of her most iconic looks of the series.
She totally pulled off the suit she wore when she was her grandfather’s best man.
When Richard asked Rory to be his best “man” for his vow renewal ceremony, she took the role very seriously – which included donning a full suit and tie for the event.
She was poised and professional during her first newspaper internship.
Rory was always a very put-together college student, but she stepped up her game when she started interning at Logan’s father’s newspaper.
This blue cardigan over a white blouse and grey dress pants screamed young professional.
She looked lovely in this black dress and heels.
A big part of Rory’s wardrobe change happened when she was distancing herself from Lorelei, and this black dress is a prime example.
Despite being outside of her normal style, the lace overlay and bow heels were a fun touch.
She looked super sophisticated and chic in this Chanel-like blazer.
In college, Rory was all about slim jeans and fitted blazers, and this outfit is a great example of it.
She looked trendy and very put together in this Chanel-like blazer and brown corduroys.
Rory’s outfits continued to mature when she was living with and working for her grandmother.
Some of Rory’s outfits were chicer, and others were a little more conservative.
Take this one, which is one of the sophisticated looks Rory wore during her break from Yale when she was living at her grandparents’ house.
Rory definitely looked the part at the USO event she planned.
When Rory started helping her grandmother plan events for the Daughters of the American Revolution, she didn’t shy away from going all-in on a theme.
For the USO party, she donned a full uniform, retro waves, and a bold lip.
She seemed more like herself in this simple jeans and sweater combo.
This was a classic Rory look – a cute but understated sweater and a pair of comfortable-looking jeans. It’s simple, but it really works.
It was also nice to see after a season of more sophisticated outfits because it felt much truer to the character.
Rory always knows how to layer.
Rory’s style throughout her college years was in flux, but once she returned to her cosy wardrobe it felt right.
This turtleneck and wool dress ensemble was stylish without being overly stuffy.
She looked sophisticated for her graduation celebration.
After years of dinners and events at the grandparents’ house, Rory definitely developed an eye for formal attire.
This simple, but elegant, gold jacket that she wore to her graduation celebration definitely made her look like a sophisticated young adult.
Rory was back in cosy cardigans for her last outfit of the series.
At her core, Rory is all about being cosy and comfortable. No matter how much her wardrobe evolved throughout the series, the last outfit she wore on the original show went back to her roots.
The short-sleeved cardigan and simple button-up shirt seemed like classic Rory.
- THEN AND NOW: ‘Gilmore Girls’ characters on their first and last episodes
- 15 things you probably didn’t know about ‘Gilmore Girls’
- 17 celebrities you probably forgot appeared on ‘Gilmore Girls’
- 10 errors and plot holes you never noticed on ‘Gilmore Girls’
Business Insider Emails & Alerts
Site highlights each day to your inbox.