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Dress Like a Gilmore S1 E1

I’m starting a new series today that’s perhaps a little ridiculous but I thought it would be fun none the less. In the Dress Like a Gilmore Series I am going to be blogging through the fashions of the series Gilmore Girls. Yes, this series is long gone and as the Gen Z people would say it’s a little “cheugy”. But for geriatric millennials women like myself this series is a form of comfort food that many of us like to watch in the fall/winter when it’s cold outside.

Gilmore Girls DVDS

The characters are definitely flawed in Gilmore Girls but a lot of what I love about the series is the witty writing, the strong ensemble cast, and the fun feel of a crazy small town. It is upbeat and often a little ridiculous which is part of why it makes such a great comfort watch. There’s also a huge nostalgia factor here for me. When the series began I was a junior in high school and so honestly I kind of grew up along side of Rory and the show just very much feels like that time of my life in high school and college.

Gilmore Girls Closing

I was inspired by an Instagram account I saw from Larisa who is cooking her way through the Gilmore Girls series which sounds quite fun so if you are at all interested in that you can follow along with her on Instagram or her blog.

So here’s how the series will go. I am watching through Gilmore Girls currently while I walk on the treadmill and I’m pausing periodically to snap photos of the clothes I love. Then I’ll share those snaps along with links to where you can get items to copy the looks and some of my general thoughts about the episode. Let’s get started!

Season 1 Episode 1

Quick Recap

We get to meet the girls, a few people from Stars Hollow, and Richard and Emily. Rory gets accepted to Chilton and then waffles about that decision when she meets Dean. Lorelai figures out a way to pay for Chilton and she and Rory begin having Friday Night Dinners with Richard and Emily.


I’m not going to cover every outfit in the series, I’m just going to highlight ones that I really like. And I’m going to add links to the items that I’m sharing. Obviously these won’t be the ones actually on the show but things that I think are similar but somewhat updated as well.

Coffee Please

Since the girls live in Connecticut they have lots of cold weather clothes and accessories. I love this hat.

The MooMoo Sweater

Lorelai calls this a Moo Moo but I love an oversized chunky sweater in the fall. I also love Rory’s classic leather book bag.

Last Day at Stars Hollow High

Rory’s outfit is very 2000. I’m not sure I can pull this off these days but I still love it.

Chambray + Dress

Sookie is limited half the time by having to wear chef’s uniforms but I love her off duty style. I still love a chambray top and throwing it over a cute dress is a fun look.

Random Thoughts

  • The episode opens with the song “There She Goes” as Lorelai walks to Lukes. It’s just such a vibe as they say. That song and the feel of the beginning is just such a feeling of the nostalgia why many of us like to rewatch the show. It feels comfortable and bright and fun. It’s also perfect for someone like me who likes to have tv on in the background while I work.
  • Drella is the absolute best. I love Alex Borstein.
  • Mrs. Kim trying to find the girls in the antique shop and the back and forth is just one of those silly scenes that I love.
  • I haven’t watched Gilmore Girls in a while and when I first saw Edward Hermann and Kelly Bishop this go around I thought they’re so young in the first episode. In my head when I picture them I think I typically think of how they look a bit later in the series. Both of them are such good looking people and I love them as Richard and Emily.
  • I love how “welcome to our little corner of the world” plays as the episode closes. The town of Stars Hollow and it’s somewhat cooky residents are a huge part of why I love the show.
  • I don’t necessarily love all the clothes, some of them were trendy for the time but I still love a lot of them. The heart wants what the heart wants.

Do you like Gilmore Girls? Let me know if you do and if you have any thoughts about the episode, the clothes, etc. in the comments below!

Mary Martha Mama