Cozy Knits & Preppy Staples: How to Dress Like Rory Gilmore

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Discover how to dress like Rory Gilmore effortlessly with our expert tips. Unlock the secrets to Rory’s iconic style today!

Although it ended in 2007, Gilmore Girls was a TV favorite of daughters and moms alike for seven seasons (and a revival series). Set in a small Connecticut town, the hit CW series followed Lorelai and her daughter Rory through Rory’s time in high school and college. The dialogue was fast-paced and filled with pop-culture references, and the girls both had family, relationship and career highs and lows.

To this day, the comedy-drama is a must see show, and Rory’s looks are still perfect style inspiration for any college student. Below, we’ll show you three college style tips inspired by Rory Gilmore’s wardrobe.

Rory’s Style: The Basics

Through her awkward high school years, to her prep school uniforms, to her time at Yale, Rory’s style matured from t-shirts and jeans to cardigans and dresses. Her polished, sophisticated wardrobe choices perfectly reflected her dedication to succeeding in the world of journalism and achieving perfect grades.

With graduation season fast approaching, Rory’s chic, ladylike looks are the perfect inspiration for parties, interviews and end-of-the-year events. Read on to learn how to get them for yourself.

1. Try Ladylike Silhouettes

Try Ladylike Silhouettes

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Whether you credit her high-society grandparents or her private school days, Rory’s wardrobe always revolved around classic, ladylike pieces. For family dinners, work events and days at the office, her go-tos included a-line skirts, collared blouses, cardigans and fitted (but conservative) dresses.

Rory’s ladylike aesthetic is perfect for college students who want to look a little more polished in their everyday lives. If a long skirt and cardigan are a little too matronly for your liking, choose one of the pieces (an a-line skirt, collared blouse, or cardigan) and mix it with a favorite top or pair of jeans. A basic string of pearls is also a great way to add a bit of classic femininity to any outfit.

Also Read: I Dressed like Gilmore Girls: A Year in the Life Characters for a Week

2. Make Simple Dresses Your Closet Staples

Make Simple Dresses Your Closet Staples

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One of the best college-girl closet staples is a comfortable, stylish dress. As we all know, a pretty cotton dress is easy to dress up or down for almost any occasion. And Rory definitely knew this – as she transitioned from high school to college, she branched out from jeans and polo shirts to modern and classic frocks.

So embrace the versatility of the classic dress: Pair a black cotton dress with a denim jacket and flats for a day of classes, then lose the jacket and add a great pair of heels for a night out. Channel Rory’s style by choosing simple dresses in neutral colors like navy blue and black – they’re both timeless and flattering.

3. Invest in Polished Basics, then Mix & Match!

Invest in Polished Basics, then Mix & Match!

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While her style matured over the years, Rory was always a jeans-and-t-shirt girl at heart. However, jeans and a tee just don’t cut it when you want to look put-together and professional. So when Rory got to Yale, she depended on sweaters and blazers to add polish to her teenage wardrobe staples.

Hopefully, you already have a great mix of basic t-shirts, tanks and jeans in your wardrobe, but to really step up your style, don’t wear them on their own. The key is to pair these basics with something a little more grown-up, like a nice sweater or structured jacket.

As Rory proves, whether you rock a well-cut blazer with a t-shirt and Converse or a pretty tank with a chunky knit sweater, mixing and matching can have great results!

Also Read: College Style Tips Inspired by Lorelai Gilmore from Gilmore Girls

Channel Your Inner Rory Gilmore: Style Tips Inspired by Stars Hollow’s Favorite Bookworm

Rory Gilmore: queen of cozy sweaters, witty comebacks, and effortlessly chic outfits. Whether you’re a bookworm longing for Stars Hollow charm or simply aiming for a timeless and versatile look, Rory’s wardrobe offers endless inspiration. 

Here are some tips and recommendations to channel your inner Rory:

Cozy Classics:

  • Get cozy with chunky knit sweaters in those earthy tones like cream, beige, and brown. They’re perfect with jeans or a corduroy skirt, giving you that classic fall vibe.
  • Layer a crisp white button-down shirt under your sweater or vest to add a bit of a preppy feel. And don’t forget to roll up your sleeves for a relaxed vibe.
  • For that extra dose of coziness, try corduroy pants, skirts, or jackets in warm jewel tone colors like olive green, burgundy, or deep mustard.

Preppy Chic:

  • Add some preppiness to your look with a sharp blazer in navy, grey, or plaid. Throw it over a sweater for prep school vibes or pair it with a blouse and skirt for a polished date night outfit.
  • Embrace the preppy vibe with a classic polo shirt. Rory loves her polos! Tuck one into jeans or skirts to add a sporty yet sophisticated touch, and toss on a cardigan for extra coziness.
  • Show off your figure with a timeless A-line skirt, whether it’s in floral prints, corduroy, or denim. Match it with a fitted sweater or a tucked-in blouse for that effortlessly put-together look.

Accessorize Like a Gilmore:

  • Grab a structured satchel or canvas tote bag for style and practicality. A fun scarf or a cute bag charm can always add a splash of color.
  • Channel Rory’s feminine style with delicate pearl necklaces or earrings. Layer them with other necklaces for a unique touch.
  • Go full-on preppy with a classic headband. Whether it’s made of fabric or adorned with pearls, Rory will approve.

So, grab a cup of coffee and a good book, and let Rory Gilmore be your style guide. Rock your cozy classics, add a dash of preppy chic, and accessorize with classic jewelry. Remember, it’s all about feeling confident, put-together, and ready to conquer the day, Stars Hollow style!

Also Read: I Dressed Like Gilmore Girls Characters for a Week & Here’s What Happened

What do you think about these Rory Gilmore outfits?

Over the seven seasons of Gilmore Girls, Rory’s style evolved as she did, transforming her from an awkward high school student to a self-assured, successful undergrad at Yale. Rory’s looks are ladylike and conservative while still being casual and accessible – the perfect combination for college girls wishing to step up their style.

So what do you think of Rory’s style? How did you create a more grown-up wardrobe when transitioning from high school to college? How do you add polish to your ensembles?

I love to hear you feedback and requests for future posts – be sure to leave a comment!

4 thoughts on “Cozy Knits & Preppy Staples: How to Dress Like Rory Gilmore”

  1. I loved this post. I am a gilmore girl addict and needed some outfit ideas. I also linked it on my blog hope thats ok!


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