The 10 Best Fashion Moments on Gilmore Girls, and How to Re-Create Them Inline

  • Image may contain Clothing Apparel Dress Human Person Evening Dress Fashion Gown and Robe
    Photo: Courtesy of The WB
    1/20

    In 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.

  • This image may contain Clothing Apparel Dress Fashion and Robe
    Photo: (Clockwise from top left) Courtesy of matchesfashion.com; Courtesy of yoox.com; Courtesy of farfetch.com
    2/20

    Sies 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

  • Image may contain Human Person Clothing Apparel Lighting Sleeve and Long Sleeve
    Photo: Courtesy of The WB
    3/20

    I’m not sure what’s funnier—Lorelai and her mother Emily’s matching red jackets, or Emily dance-walking on the runway?

  • Image may contain Clothing Apparel Blazer Coat Jacket Overcoat Suit and Tuxedo
    Photo: (Clockwise from top left) Courtesy of modaoperandi.com; Courtesy of whitehouseblackmarket.com
    4/20

    Blaze Milano MMM by Night blazer, $2,070, modaoperandi.com; White House Black Market suede belt, $64, whitehouseblackmarket.com

  • Image may contain Dance Pose Leisure Activities Human Person Dress Clothing Apparel Fashion Evening Dress and Gown
    Photo: Courtesy of The WB
    5/20

    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.