Fashion

Now That I’m in My 30s, I Just Want to Dress Like Lorelai Gilmore

Leather blazers and pencil skirts ahead

Stephanie Maida

By Stephanie Maida

Published Sep 2, 2025

PureWow editors select every item that appears on this page, and some items may be gifted to us. Additionally, PureWow may earn compensation through affiliate links within the story. All prices are accurate upon date of publish. You can learn more about the affiliate process here.

Lorelai Gilmore Style: Collage featuring Lorelai and Rory Gilmore from 'Gilmore Girls' and fall clothes inspired by the character

Binge watching Gilmore Girls is a rite of passage for every precocious 12th grader (both past and present), who can take pride in keeping up with the characters’ quips and, if not somewhat smugly, think to themselves, “I understood that reference.” As is, of course, the inevitable idolization of Rory Gilmore’s wardrobe. The picture of Connecticut prep, our young heroine dons cozy cable-knit sweaters, plaid skirts and prim cardigans that are just begging for a study sesh in the hallowed halls of an Ivy League library (Yale’s, that is, in her case). Indeed, her cult-loved style is the sartorial embodiment of scholarly, and something I, too, lusted after throughout my teens and 20s.

But now, in the midst of my umpteenth rewatch of the series at the ripe (not old) age of 34, I realize what I should’ve seen all along: Lorelai Gilmore is the real style icon of the show. Say what you will about her frazzled, sometimes frivolous nature (which, admittedly, I can relate to), but when push comes to shove, no one can play the part of a posh professional who totally has her sh*t together better—at least in terms of her fashion sense.

Lorelai’s rotation of sleek pencil skirts and sophisticated blazers scream ‘90s Ralph Lauren core, though her collection of quirky, kitschy and distinctly Y2K whimsigoth looks are not to be overshadowed. Together, they create the closet of the grownup I used to imagine I would be back when the show first aired in the early 2000s; chic but not stuffy, fun but not frilly. And seeing as I’m currently around Lorelai’s age in the early seasons, I find myself drawn to her looks more than ever—so what better time to embrace them than the fall, aka the official season of all things Gilmore?

Ahead, I’ve rounded 11 pieces that seem like they were plucked straight from her wardrobe—and will soon be added to mine.

Want to know which buzzy products are *really* worth buying? Sign up for our shopping newsletter to uncover our favorite finds.

Senior Commerce Editor

Stephanie Maida

Senior Commerce Editor

  • Oversees PureWow's coverage of sales and deals, celebrity commerce and new launches across categories
  • Has worked as a writer and editor for 10+ years
  • Studied journalism at New York University

read full bio