Gilmore Girls Inspired Lookbook

Welcome back to The Sims Resource! I’m excited to announce that it is, indeed, fall. And as we all know, fall is the time to start rewatching Gilmore Girls. At some point, the entire internet decided that the show has decidedly fall-inspired vibes, which makes it the perfect cozy show to watch as temperatures drop (if you live somewhere that has seasons) or while you pretend the temperatures are dropping. Let’s get into some Gilmore inspired fashions – tis the season!

Lorelai

Listen. Lorelai Gilmore is a legend, and an icon, and I’m definitely not just saying this because I’m wearing a tee shirt with her face on it at this very moment. (Okay, maybe I am. And it’s a very good shirt). I love Lorelai as a character. She’s probably one of the most iconic TV heroines of the 21st century, and I’m really happy that I got to discover the show on Netflix in the past year, because Lorelai is a fascinating character to watch, but above all is entertaining. Her fast-talking jokes are probably my favorite style of writing in any show, and Lauren Graham is incredible at delivering them. The role truly wouldn’t be the same without her.

In terms of styling Lorelai, I had a lot of options. She’s sort of known for having an insane sense of style and some of the most quintessential early aughts looks out there. She rocked a lot of low rise jeans, baby tees, and bandanas and hats that truly fit the era. If you want y2k fashion, Lorelai Gilmore is absolutely your girl. I went for a pretty typical look for her, though I definitely did consider using one of her work outfits or even a formal dress. Lorelai mastered the “professional yet cute” look whenever she was at the inn, so if I ever get a chance to do another one of these I might have to put together one of those. Her formal dresses were usually to die for, too (once you get rid of those awful boleros. That’s one y2k trend I will not abide by).

Rory

Rory Gilmore is a hotly disputed character in some circles, but in the show’s early seasons she was truly one of the most beloved teens on TV. Truly meant for the Bookworm trait, Rory is rarely seen without a book in her hand or a reference to share. I really love Rory, and watching her grow up is meaningful as someone who’s been in a lot of the same spots she’s been in. Her high school graduation speech? I well up with tears every single time I see it, even though I know it’s coming. Alexis Bledel defined the role with her quiet charisma and charming naivete (“I’m winningly naive!” – if you know, you know).

For Rory’s outfit, I went with her most iconic outfit. The Chilton uniforms were reportedly designed based off Alexis Bledel’s eyes, which explains why they’re such a pretty shade of blue. I went with a blue and red uniform in my game because it was the closest I could get to Rory’s actual uniform. I also have to praise how realistic of a uniform it is. A lot of other teen shows take a lot of liberties with school uniforms, and while that kind of escapism is fun, it really grounds Gilmore Girls to have Chilton with very standard high school uniforms that have mix and match pieces to wear. I went with my favorite version here–the navy blazer is absolutely my style, but the sweater vests are definitely a close second. Preppy fashion! It’s timeless.

Emily

Emily Gilmore is perhaps the most interesting Gilmore Girl in a lot of ways. The arc she undergoes throughout the show is really interesting to watch (though I won’t get into specifics here!) and the performance of the character by Kelly Bishop is truly a highlight in a show full of top notch actors. Emily is hard to deal with, manipulative, and cruel; but she can also be kind, thoughtful, and comforting. Watching her flip on a dime between the two is always interesting, even though it definitely hurts when you as the viewer know she’s doing the wrong thing. She’s an anti-hero in Chanel No. 5 – an unexpected combo, but just as fascinating as any other anti-hero out there.

I debated between dressing Emily in one of her coordinated tweed sets or with a dress and jacket combo, but I ultimately decided on the latter because I’ve always enjoyed her dresses and skirts a bit more than her pantsuits. I went with green because of an image I saw of her in a mint colored sweater, though I considered a pink dress and jacket too. I love when Emily wears color. Too many redheads shy away from bright colors for fear of clashing, but I love the combination (even if Emily’s hair is a pretty dark red). I gave her a small necklace instead of her pearls, but I debated between the two for a while. I ultimately went with the necklace because I liked it more with the dress, though let it be known that Emily Gilmore is nothing without her pearls.

Lane

Lane is one of the sweetest, funniest characters on Gilmore Girls. She’s a ray of sunshine even when her circumstances are dire and she’s a great drummer once she finds her true calling. I love how passionate Lane is about her music, even through hard times and doubts. She’s a role model for perseverance and following your dreams. Lane could have felt like one of the kooky townspeople and lacked depth, but between Keiko Agena’s performance and real-life stories from producer Helen Pai (on whom Lane’s character is based), she practically jumps off the screen in all of her bubbliness and joy.

I went with one of Lane’s performance outfits for this lookbook because I think they’re some of my favorite in the show. She obviously takes inspiration from early 2000s style, but she also manages to bring in some classic rock and roll influences while also staying true to herself (by keeping her glasses on! Glasses may not be hardcore rock, but they are hardcore Lane). The flouncy layered skirts paired with tee shirts and mesh sleeves are even seen on pop stars like Olivia Rodrigo today, proving that Lane is nothing if not a trendsetter, even if her day-to-day clothes are a lot more cutesy and simple (though they have their own charm). Honestly, Lane is making me want to go buy a mesh shirt to layer under things, even though I’m a complete prep and it wouldn’t work for me at all. She’s just that much of a style icon!

Thanks for checking out this Gilmore Girls inspired l! If you liked this blog, check out Room Reno #65: Sunny Living Room or a Back to School CAS Showcase. Looking for something else? Read about the CAS from our K-Pop Collection or about the latest game updates! Have a great day 😎