Gilmore Girls: 5 Times Rory Dressed Like A Millennial (& 5 Times Like Gen Z)

From the moment Rory came waltzing into Luke’s Diner on Gilmore Girls, audiences could see that she was a young woman with an impeccable sense of fashion. While Rory was more interested in her books, she still took the time to express herself through clothing.

Rory was never out of style on Gilmore Girls. She channeled her creativity anytime and anywhere. While Rory is a millennial, she definitely was comfortable with what would become Gen Z fashion trends as well. With ensembles this much on point, Rory made anything look cool, no matter what generation it belonged to.

Dressed Like A Millennial

Cerulean Sweater

Gilmore Girls is full of Rory’s fashion hits and misses from the get-go until the very end. Speaking of the former, the millennial audiences find it adorable that she’s wearing a cerulean sweater on a workday.

She looked well-put-together in this business-as-usual outfit in “How Many Kropogs to Cape Cod?” Rory’s cerulean cardigan and a hard-to-impress boss give a distinctive The Devil Wears Prada vibe. Viewers absolutely endorse this millennial shade of blue. Quite frankly, the only thing missing from the scene is Miranda Priestly’s cerulean sweater monologue.

Millennial Pink Blouse

Rory also rocked a millennial pink blouse midway through her internship at the Stamford Eagle Gazette. She paired the top with a knee-length skirt and styled her hair back with a headband.

This fashion moment from “Blame Booze and Melville” is a throwback to Rory’s headband years at Chilton. She was smart enough to know that the office dress code wasn’t to be trifled with and bold enough to experiment with the trendy millennial pink color.

Sharp Skirt Suit

Rory’s sharp fit suit and slick ponytail in “How Many Kropogs to Cape Cod?” added so much detail to her character. She wore it on her first day at the Stamford Eagle Gazette because she wanted to impress everyone, especially the owner, Mitchum Huntzberger.

Rory showed up at work in fine-tailored clothing that’s had its moments, especially with the millennial cohort. With a chic suit like that, she lived well up to her reputation as a millennial go-getter. Rory would have served fans more looks had the show not dropped the Stamford Eagle Gazette storyline so abruptly.

Pink Top

Lorelai leaving town with Rory to avoid her wedding (and deny an explanation to Max Medina) is definitely an illogical aspect of her dating life. Nevertheless, the mother-daughter duo made a memorable trip out of it, which included a visit to Harvard.

Fans noticed Rory’s personal brand of millennial dressing in “The Road Trip To Harvard.” She’d clubbed her flattering pink top with dark blue jeans. To pull off the look, she tied a grey sweatshirt around her waist. Rory definitely took a risk with the unconventional sweatshirt tie, but what matters is that millennials wholeheartedly approve of it.

Chic Blazer

Rory looks quite the quintessential millennial in season 6’s “Let Me Hear Your Balalaikas Ringing Out.” She pairs the fitted tweed blazer with black pants and kitten pumps. This sophisticated, and elegant outfit is perfect for a night out with her former flame, Jess, and her current boyfriend, Logan.

With bangs and waves loosened-up waves, fans can tell Rory has that chic college-woman vibe going on in the episode. Her millennial fanbase one-hundred percent endorses this impeccable fashion moment.

Dressed Like Gen Z

That Chunky Creme Sweater

Chunky sweaters epitomize comfort wear, and Rory was one step ahead of the curve back in 2000 with this oversized slouchy piece. She completed the outfit with bootcut jeans, chunky black shoes, and a cord necklace.

Rory let her hair open, which was an added delight and a perfect representation of who she was in the early years. Rory’s look from Gilmore Girls’ pilot episode is one for the books. It’s youthful, effortless, and essentially the everyday-wear look that Gen Z prefers.

That Yale Baseball Cap And Parka

The baseball cap is a favorite among Gen Z and has been trending for a couple of years now. Rory wore the classic Yale headgear while working as a card swiper at the Yale dining hall in “The Incredible Sinking Lorelais.” The cap, combined with the black jacket, and the skin-colored shirt made for a cool college-woman aesthetic.

Rory was settling into Yale life and trying her best to match up to Richard Gilmore’s legacy. She didn’t want to look like she was trying too hard to fit in. Her ensemble gave the message that she was adjusting well to campus life.

Turtleneck And Flared Jeans

The Gen Z adores this comfy and well-fitted turtleneck and jeans combo from “Scene In A Mall.” There’s no denying Rory’s Yale look became cooler, chicer, and elegant as time passed. Her bob gave a character to the outfit and fans are convinced only she could have pulled off the preppy vibe.

Rory’s full-on monochromatic look is effortless and counted among her best outfits. She was recovering from a cold in the episode and what better than a cozy turtleneck to convey that message?

That Cardigan

Y2K fashion made a comeback in 2021 by courtesy of Gen Z. One of the staples from that trend, predicted to continue into 2022 is the good-old cardigan.

Rory wore cardigans on various occasions in the show. She’s a sad person in “A Messenger, Nothing More,” but not out of fashion with that polka dot cardigan of hers. The outfit is a palette of earthy, calming, and grounding hues and Gen Z fans are here for it.

Elevated Basics

Elevated basics are at the heart of Gen Z fashion. They look versatile, functional, practical, and high-quality. The Gilmore Girls star, Rory, evidently knew how to elevate something as basic as her Chilton uniform.

In season 1’s memorable episode, “Kiss and Tell” she paired her light blue shirt with an oversized black blazer. Her plaid skirt was cut to a high waist and her shirt was neatly tucked inside.  The new oversized clothing trend isn’t going anywhere, and Gen Z adores Rory for this outfit.

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