Rory Gilmore's Top Ten Outfits From "Gilmore Girls"

Updated on September 22, 2019
Rachel M Johnson profile image

Rachel M. Johnson is a lover of all things pop culture. She's been writing about music and entertainment online for over two years.

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Gilmore Girls is a beloved feel good show that introduced the world to the fast talking, coffee loving mother/daughter duo Lorelai and Rory Gilmore. Fans were able to see Rory blossom and mature throughout the series, both in style and beauty. Like her mother, Rory's fashion was truly something to behold. Let's take a closer look at Rory Gilmore's most iconic fashion moments.

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10. Lover of the Cardigan

One clothing item that seemed to stay a staple in Rory's style was a cardigan. She wore many at the beginning of the series and all throughout the course of the show. Whether she paired it with a simple dress, cute blouse and jeans or fun t-shirt, her cardigan collection was on full display. In the later seasons, Rory's style began to grow more sophisticated and refined, as reflected in her elevated attire. Her clothing became more chic, and often she'd wear feminine blouses and dresses paired with an elegant cardigan.

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9. Rory's Cotillion Ball Gown

Rory was truly a vision in white when she wore this tightly-fitted bodice ball gown for her introduction to society. She looked just like a modern day princess with the elegantly detailed bodice and matching opera gloves, and with her hair swept back in a delicate bun Rory was a true star at the cotillion. Her make-up was natural and fresh and she wore a simple pair of studded earrings as her accessory of choice. Her escort Dean looked handsome in his tuxedo and bow tie, and together they made quite the dapper pair. It was in this moment that Rory truly got a taste of what it meant to be a Gilmore.

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8. Sweater Weather

You knew that fall was in the air whenever you saw Rory sporting one of her many cozy sweaters. Both of our favorite Gilmores knew how to embrace the fashion of the seasons, and Rory was easily able to play up all of her sweaters. Whether she was rocking one with a simple pair of denim jeans or a cute skirt and chic boots, her love of all things knit was on full display. Rory would often accessorize with her ever-present scarf and hat collection, making you really want to get a cup of Luke's coffee and curl up with a good book.

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7. The Daughter of the Revolution Dress

Rory looks like she stepped right out of the 1940's in this USO inspired uniform for the DAR bash she threw in Season 6. The cute and vintage uniform and hat fit her like a glove, and her tightly curled and pinned hair only further elevated the look. With her bold red lip and glamorous make-up, Rory would have easily fit in back in that time. The whole party and episode had an old Hollywood-Casablanca vibe, and the Andrew Sisters soundtrack truly captured the essence and feel of the time. Rory definitely stood out in the costume and looked absolutely stunning.

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6. Rory's Chilton Dance Dress

For her first ever school dance, Rory was the epitome of elegance when she wore this beautiful off the shoulder gown handmade by Lorelai. The satin bodice was the perfect shade of purple, while the tulle bottom flared out at a chic tea length, A-line silhouette. Her hair was swept back in a sophisticated up-do, while a delicate necklace adorns her and paired perfectly with the simple earrings. Not only did we get to see Rory all dressed up, but she was able to show off her cool-drink-of-water boyfriend Dean to her fellow classmates.

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5. Chic Coat Collection

It's no secret that both Rory and Lorelai have an impressive and enviable coat collection; their colorful outerwear is fully on display throughout the course of the series. Just like her mom, Rory always utilizes each and every one of her coats. She often opts to wear a chic peacoat, as shown with her long, deep burgundy number she wore many times. Rory also was a lover of denim, as she sported jean jackets and trench coats with dresses, blouses and boots. She was very talented at properly pairing her many gorgeous coats with just the right outfits.

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4. Dresses Galore

Just like her mother, Rory developed a fondness for a killer dress early on. During the beginning of the series she would often wear simple dresses with a cardigan, but as the show progressed her dress style got more daring. Rory embraced unique patterns and elegant silhouettes and colors, demonstrating just how much her fashion was elevating. Many of the dresses had delicate patterns and she always looked chic and sophisticated. Her dresses also got a little sexier when she started dating Logan, and she truly came into her own.

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3. Vintage 1940's Dance Marathon Dress

Rory looked like a retro-queen when she wore this vintage red polka dot dress with three-quarter sleeves to the Stars Hollow dance marathon. With her hair curled and pinned back in a demure and classic style, she opted for a matching bold red lip and dramatic eye make-up. Delicate earrings and a matching necklace completed the look and really pulled it all together. Though the premise of the episode was fun, with Lorelai and Rory as dance partners, the ending left everyone in tears. Dean broke up with Rory because of her feelings for Jess, in front of the people of Stars Hollow.

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2. Rory's Chilton Uniform

Of course Rory's iconic Chilton uniform was going to be on this list. Her jacket, button up shirt and plaid skirt became a staple for the driven student, and she wore it constantly throughout the first three seasons. While there is only so much you can do with a uniform, Rory made it her own by pairing it with black tights, colorful scarves and hats and cute coats. She was also able to utilize the outfit once more in Season 5, when she again donned the getup for a Pulp Fiction party. Rory dressed up as Gogo Yubari and even rocked a fun, black wig.

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1. The Life and Death Brigade Gown

Rory was absolutely radiant when she wore this gorgeous, powder blue strapless floral ball gown in Season 5. In the episode, our favorite Yale reporter delves deep into the mysterious secret society of the Life and Death Brigade, headed by the handsome Logan Huntzberger. Rory looked stunning in the gown, with her curled shoulder length hair and matching wrap. Her blue eyes truly popped in the shade and looked both sweet and sassy all at the same time. Who could possibly forget the iconic "You jump, I jump Jack" line she spoke before bungeeing off the platform, holding an umbrella and the hand of Logan? What a perfect moment!

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    © 2019 Rachel M Johnson

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