21 of Rory Gilmore's most iconic outfits on 'Gilmore Girls'

Warner Bros.Throughout her years on the show, Rory Gilmore debuted some iconic looks.

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.

Warner Bros.Rory was comfy in a chunky sweater on the series’ pilot episode.

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.

Warner Bros.Rory rocked the uniform for the first time on season one.

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.

Warner Bros.Rory sported a ridiculous hat while playing golf.

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.

Warner Bros.Rory wore this blue dress to a school dance during season one.

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.

Warner Bros.Rory was presented to society in a big white gown.

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.

Warner Bros.Rory wore this costume when she played Juliet at Chilton.

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.

Warner Bros.Lorelai and Rory both rocked polka-dot dresses and vintage hairdos.

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.

Warner Bros.Rory always knew how to pull off a fall look.

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.

Warner Bros.Rory’s bob and turtleneck showed a bit of a fashion evolution.

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.

Warner Bros.She reenacted the ‘Portrait of a Young Girl Named Antea.’

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.

Warner Bros.Rory had to wear the dress for one of Logan’s secret society events.

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.

Warner Bros.Rory wore a suit for her grandparents’ vow renewal.

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.

Warner Bros.Rory always knew how to rock business casual.

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.

Warner Bros.Rory and Lorelai may have been having an awkward conversation, but they looked great.

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.

Warner Bros.Rory really changed her wardrobe when she was living with her grandparents.

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.

Warner Bros.Rory looked like a sophisticated young woman in cardigans and structured skirts.

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.

Warner Bros.Rory planned the event for the Daughters of the American Revolution.

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.

Warner Bros.Rory ditched the structured blazers for a more casual look.

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.

Warner Bros.Rory’s fall looks just kept getting better.

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.

Warner Bros.Rory could definitely put together a formal outfit by the end of the series.

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.

Warner Bros.Rory’s last outfit on ‘Gilmore Girls.’

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.

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