gilmore girls fashion moments© Instagram

13 Of The Most Iconic Fashion Moments On Gilmore Girls

Fifteen years have come and gone since the Gilmore Girls made their last coffee run in the cosy town of Stars Hollow. But even after all this time, the cultural impact of this beloved mother-daughter duo continues to thrive, especially in the world of fashion.

Creator Amy Sherman-Palladino’s idyllic vision of small-town Connecticut living has left a lasting impression, inspiring countless fashion trends and influencing the style choices of many. The witty banter and charming romance of the show still resonate today, reminding us of the power of a strong bond between loved ones. From Lorelai’s signature quirky ensembles to Rory’s classic preppy looks, the Gilmore Girls’ fashion legacy lives on.

Both Lorelai and Rory have become icons of a certain kind of noughties style, one marked by low-rise jeans, autumnal sweaters, private school uniforms, and so much denim. You can’t scroll through a Y2K fashion board on Pinterest without encountering stills from the show.

On TikTok and Instagram, creators rack up views on videos showing what they would wear in Stars Hollow, whether for going on a bookstore date or grabbing late-night java at Luke’s Cafe. There’s something about Gilmore Girls’ fashion that particularly resonates with Gen Z—most of whom weren’t born yet when the show’s first season premiered.

Ahead, we call out 13 of our favorite fashion moments from the iconic show.

Rory’s Gingham Dress

In season one, Rory re-creates The Donna Reed Show for her boyfriend, Dean. To play Donna, the show’s chipper, idealised housewife, she wore an orange full-skirted gingham dress with a headband and apron.

Lorelai & Rory’s Vintage Costumes

Where do Lorelai and Rory hide all of these amazing vintage costumes? For the town’s retro-theme dance marathon, Lorelai wore a stunning black halter dress; Rory went with a sweet polka-dotted number.

Lorelai’s Juicy Couture Tracks

Nearly two decades later, Lorelai’s Juicy Couture track pants are back on trend. Never forget the moment when she turned around and her mother, Emily, said, “You have the word ‘juicy’ on your rear!”

Lorelai’s Pink Coat

Gilmore Girls fans will know this coat as “the pink coat.” It made thousands of girls (us included) want a Pepto-pink coat, and at the time, they were few and far between. Now, pink coats are a dime a dozen, but they’ll always remind us of Lorelai.

Rory’s Ball Gown

Love him or hate him, Logan took Rory on some pretty amazing adventures. Early in their relationship, she accompanies him to an event for the Life and Death Brigade, a Yale secret society, and every girl has to wear a ball gown. Rory’s is pale blue, like Cinderella’s.

Rory’s Tuxedo

Rory’s Tuxedo©IMDb

When Lorelai’s parents, Richard and Emily, decide to renew their vows in a big way, Richard asks Rory to be his “best man.” She looks cooler than ever in a tailored tuxedo and loose chignon.

Lorelai’s Shiny Slip Dress & Cardigan

Lorelai’s Shiny Slip Dress & Cardigan©IMDb

For her walk down the aisle, Lorelai wore an iridescent slip dress and sequined cardigan—two items we wouldn’t mind having in our closets now.

Lorelai’s Floral Dress

gilmore girls fashion moments©IMDb

Season seven—also known as the final season of Gilmore Girls because we don’t speak of the disappointing revival ‘A Year In The Life’ here—had some of Lorelai and Rory’s best looks. We wouldn’t mind owning this ’40s-ish floral dress right about now.

Jess’ Leather Jacket

Luke’s nephew and Rory’s longtime admirer-slash-lover Jess Mariano (also technically her step brother at one point but that never seems to matter in teen dramas, does it?) undergoes a real style evolution as he grows up. When he arrives in Stars Hollow, he’s an apathetic bad boy usually seen in grungy layered T-shirts, trucker jackets or double denim. Here though, in S3, he invests in a classic leather biker jacket and runs away to California, determined to track down his dad and figure his life out.

Lorelai’s Layered Tees

In S1 E15, Lorelai bails on a cute renovation date with Luke to go to Friday night dinner with her parents and, it transpires, her high school sweetheart (Rory’s dad Christopher) and his parents. Somehow this leads to Lorelai and Christopher sleeping together on the balcony of the former’s childhood bedroom. Lorelai then does what any of us would do in such a situation and breaks into Luke’s Diner and guilt-paints it. Naturally, the very DIY-phobic Lorelai doesn’t own any DIY-friendly clothes and completes the task in one of her go-to layered T-shirts and early ‘00s bandana looks instead.

Lorelai’s Cowgirl Look

In this, the second of 153 episodes, Lorelai’s furry blue alarm clock fails her and she wakes up late on Rory’s first day at Chilton, a private school in a nearby town. Realising she doesn’t have any clean clothes to wear - she was planning on wearing her “blue suit with the flippy skirt” but didn’t collect it from the dry cleaners - she instead throws on the first thing she finds: a pair of denim hotpants, a pink tie-dye T-shirt and cowboy boots. “I didn’t know the rodeo was in town,” Rory quips before they head off to school where the whole world proceeds to judge Lorelai for her on-the-spot styling decisions.

Rory’s Outfit At The Tarantino Costume Party

Back in the pilot episode of Gilmore Girls (the day before Rory started at Chilton) we saw Lorelai painting Rory’s toenails red and telling her that “private school girls are bad, and bad girls wear red polish”. Rory certainly wasn’t bad back then, but now she’s at Yale and wearing her Chilton uniform to a college party, repurposed as the ultimate bad girl: Gogo Yubari, the sadistic, meteor hammer-wielding school girl from Kill Bill. She went to the party with a boy and left having successfully regained the attention of rich boy Logan Huntzberger.

Rory’s Oversized Pilot Sweater

Back when Alexis Bledel was an extra as a “student” in Wes Anderson’s 1998 movie Rushmore, she kicked off her very first day as Rory in an oversized slouchy sweater with rolled up sleeves, a brown backpack and a cord necklace. A very ‘90s look that hung about long enough to make an appearance in this Y2K debut episode.