Fall is not just the season when I start really dressing. It’s also the time when Gilmore Girlsis on my TV, playing on a constant loop. Although the show’s main focus is the ever-changing relationship between the Gilmore family and whatever boys happen to have won Rory’s and Lorelai’s hearts that season (team Jess and Luke, forever), I think the show has some hidden fashion moments. I would love to discuss Rory’s love for oversize sweaters or Emily’s expertise in Hermès, but today’s topic of discussion is the kitschy style of Lorelai Gilmore. From the slinky slip dresses worn at Friday-night dinners to the baby tees and Bermuda shorts, her looks made sense to me despite the wild choices she made.
Unlike the rest of Gen Z, I haven’t largely resonated with the pattern-heavy and maximal style of the early aughts, but Lorelai’s outfits had this essence that always captivated me. It must have been the way she could bounce between two generations—one day emulating Rory’s style since she never got to live her own teenage years and donning a sophisticated ensemble to run her inn the next day. While I could go on about the constant juxtaposition of Lorelai’s closet, let me describe it the way she would’ve wanted—through shopping. Below, you’ll find 31 pieces that would’ve made Lorelai’s heart jump more than a cup of caffeine.