I Watch Gilmore Girls Every Fall—Here Are 8 Trends From the Show I’d Wear Today

If you also have the problem of immediately pivoting your life and re-watching Gilmore Girls the second fall rolls around, this one is for you. Although my main priorities while bingeing are enjoying Lorelai’s sarcastic commentary and watching how the girls’ love lives unfold, in this year’s rewatch, I took special notice of the fashion trends from the early 2000s that I’m seeing circling back around this season.

While a majority of people may not think of Rory Gilmore as a proposed style icon (she had enough on her résumé), she did share a closet with Lorelai, who hoarded an obscene amount of trendy clothing and could never say no to a trip to the mall. If you’re in the same boat as me and are finding yourself wanting to transport back to Y2K in Gilmore fashion, I rounded up eight of the trends that the mother-daughter duo and other Stars Hollow residents often sported along with shoppable modern versions that I’d incorporate into my wardrobe today.

From cropped cardigans to skater tees, there’s a fall item in this list you’ll want to get a hold of. Scroll below to take a trip down memory lane. Where they lead, we will follow.


Shoulder Bags

When Rory wasn’t carrying her book bag, she and Lorelai usually opted for mini shoulder bags to complete their looks. And let’s be real—they were probably filled with snacks.


Yes, I know the sweater-vests were a part of the Chilton uniform, but they were also regularly spotted across the series. What an easy way to look collegiate and stylish, no?

Squared-Toe Boots

I’d 100% wear this entire look today. It took me a closer look while watching to realize that Lorelai loved a good square toe when it came to her fall boots.


Stars Hollow loved a good tie-dye print, as I spotted the trend on characters from Lorelai all the way to Jackson and Babette.


Skater Tees

I’m sorry, but you know I had to squeeze a little Jess Mariano in the mix. (#TeamJess for life ?) While his assortment of graphic tees may not have meshed well with working at Luke’s, I know I wanted to get my hands on his collection. Whether you just want to be comfortable or incorporate that edgy aesthetic into your life, skater tees are the trend for you.

Silky Tops

Lorelai was known to always wear a trusty button-down while working at the Inn, but it was the silky numbers that really grabbed my attention.

Leather Blazers

Lorelai Gilmore wore a brown outfit with a leather blazer, so I also wore a brown outfit with a leather blazer. (But seriously, this outfit was ahead of its time.)

Cropped Cardigans

The Gilmore trio (yes, even Emily) often sported shorter cardigans over everything—from formal dresses at Friday night dinners to casual ensembles on the way to Luke’s. Either way, they’re a closet essential to own today. 



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