The 10 Best Fashion Moments on Gilmore Girls, and How to Re-Create Them Inline
Photo: Courtesy of The WB1/20In season one, Rory re-creates The Donna Reed Show for her boyfriend, Dean (who turns out to be such a wimp, but I digress). To play Donna, the show’s chipper, idealized housewife, she wore an orange full-skirted gingham dress with a headband and apron.
Photo: (Clockwise from top left) Courtesy of matchesfashion.com; Courtesy of yoox.com; Courtesy of farfetch.com2/20Sies Marjan tie-front V-neck satin dress, $948, matchesfashion.com; Dolce & Gabbana hair accessory, $35, yoox.com; Pierre Hardy curved-heel pumps, $675, farfetch.com
Photo: Courtesy of The WB3/20I’m not sure what’s funnier—Lorelai and her mother Emily’s matching red jackets, or Emily dance-walking on the runway?
Photo: (Clockwise from top left) Courtesy of modaoperandi.com; Courtesy of whitehouseblackmarket.com4/20Blaze Milano MMM by Night blazer, $2,070, modaoperandi.com; White House Black Market suede belt, $64, whitehouseblackmarket.com
Photo: Courtesy of The WB5/20Where 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.
Photo: (Clockwise from top left) Courtesy of maykool.com; Courtesy of johnlewis.com6/20Maykool polka-dot bow decor V-neck casual midi dress, $27, maykool.com; Jolie Moi lace-bonded sweetheart prom dress in navy, $85, johnlewis.com
Photo: Courtesy of The WB7/20Nearly a decade 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!”
Photo: (Clockwise from top left) Courtesy of romwe.com; Courtesy of stylebop.com8/20Romwe navy zip-up pocket hooded sweatshirt, $16, romwe.com; Juicy Couture velour track pants, $189, stylebop.com
Photo: Courtesy of The WB9/20Gilmore Girls fans will know this coat as “the pink coat.” It made thousands of girls (me 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 me of Lorelai.

Photo: Courtesy of The WB11/20Love 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.
Photo: (Clockwise from top left) Courtesy of matchesfashion.com; Courtesy of quill.com12/20The Vampire’s Wife Bonnielee cotton midi dress, $715, matchesfashion.com; Natico vented Tordado 64-inch-arc umbrella in black, $65, quill.com
Photo: Courtesy of The WB13/20When 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.
Photo: (Clockwise from top left) Courtesy of tessabit.com; Courtesy of farfetch.com; Courtesy of luisaviaroma.com; Courtesy of forzieri.com14/20Faith Connexion Serge black jacket, $508, tessabit.com; Faith Connexion wool suiting bell-bottom pants, $415, luisaviaroma.com; Lardini classic button-down shirt, $105, farfetch.com; Forzieri solid light gray extra-long tie, $78, forzieri.com
Photo: Courtesy of The WB15/20For her walk down the aisle, Lorelai wore an iridescent slipdress and sequined cardigan—two items we wouldn't mind having in our closets now.
Photo: (Clockwise from top left) Courtesy of houseoffraser.com; Courtesy of mytheresa.com;l Courtesy of neimanmarcus.com; Courtesy of efavormart.com16/20Jacquemus glitter minidress, $664, mytheresa.com; Jacques Vert sharp-edge bolero, $98, houseoffraser.co.uk; Manolo Blahnik Chaos pearly ankle-wrap sandals in black, $865
neimanmarcus.com; Efavormart six fascinating foam rose bouquets in white, $43, efavormart.com
Photo: Courtesy of The WB17/20We still aren’t sure why Rory’s upper-crust boyfriend, Logan—who is a college student, mind you—bought her a Birkin bag. Innocent Rory didn’t even know what it was.
Photo: Courtesy of therealreal.com18/20Hermès Epsom Birkin 25 bag, $11,000, therealreal.com; Hermès Taurillion Birkin 35 bag, $9,000, therealreal.com; Hermès Epsom Birkin 35 bag, $10,000, therealreal.com
Photo: Courtesy of The WB19/20Season seven—also known as the final season of Gilmore Girls—had some of Lorelai and Rory’s best looks. We wouldn’t mind owning this ’40s-ish floral dress right now.
Photo: (Clockwise from top left) Courtesy of matchesfashion.com; Courtesy of neimanmarcus.com20/20Rebecca Taylor Meadow floral sleeveless ruffled dress, $550, matchesafashion.com; Elizabeth and James Zoe large suede hobo bag in black, $595, neimanmarcus.com