If I Went Shopping With Lorelai Gilmore, I Know She’d Love These 31 Fall Finds

Fall is not just the season when I start really dressing. It’s also the time when Gilmore Girls is 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. 

Long denim skirts were a Y2K favorite, and their comeback is one I can totally get behind. If I was Rory, I’d steal this from Lorelai’s closet immediately.

A fall must-have. 

Seems appropriate for school drop-off, no? (IYKYK.)

I’m shocked this isn’t vintage.

I admired a lot of things about Lorelai’s wardrobe, but her collection of knee-high boots always caught my attention.

Regardless of how you feel about Abercrombie bringing these camis back, they serve as a reminder of a time period.

A classic pair of trousers at a great price point.

Lorelai would definitely pair this cardigan with a slip dress and mini baguette bag.

Lorelai would love this dress just as much as our editors do.

Blazers tended to be more fitted in the early 2000s, but I just know Lorelai would enjoy the current oversize-blazer trend.

Only Lorelai Gilmore and Rachel Green could convince me to wear a turtleneck.

Perfect for Friday-night dinner.

While I may not be anywhere near Stars Hollow, I can wear a thick coat, get hot coffee, and pretend like I am.

This outfit is perfect for a quick run to get a large bite at Luke’s.

Another excellent layering option for your slip dresses.

Add a pair of coordinating straight jeans and you’ve got yourself the ideal double-denim outfit.

Lorelai’s favorite denim silhouette.

Cute and practical. Your bad-hair days will thank you.

Add a silky blouse and you’re ready to run an inn.

It wouldn’t be fall in Stars Hollow without a cozy blanket scarf…

…And a cozy beanie, of course.

For the more casual days.

This sweater just seems like it was stolen right off the Gilmore Girls set.

No shortage of chunky knits here.

Add a pair of black knee-high boots for an ideal Lorelai workwear ensemble.

Sweater-vests—serving as the knitwear of choice since the 2000s.


Can you tell Lorelai’s workwear was my favorite among all her looks?

It’s hard to resist argyle print when fall comes around.

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