The Rory Gilmore Fashion Moments That Will Go Down in History

Gilmore Girls fans out there—this one's for you. Although Rory Gilmore was known for many things, we will admit that being the most on-trend girl in Stars Hallow was not her biggest priority in life, what with Chilton, Dean, Jess, Logan, Yale, Lorelai, writing, and reading every book under the sun all on her perfectly organized agenda. However, there are a few Rory Gilmore fashion moments we feel do deserve a quick round of applause.

Of course, there's the iconic Chilton uniform, featuring its dark navy blazer, plaid pleated skirt, and white knee-high socks; the darling dress she wore to help her mother (try to) win the Stars Hallow dance marathon; and (how could we forget?) her prom dress with date Dean. (Side note: Are you team Dean, Logan, or Jess?) It's Rory Gilmore fashion moments like these that have us not only stealing a few quirky styling tips for our own lives but also taking a quick trip down Gilmore Girls memory lane. Because if you know anything about the beloved series, you know it's not just a TV show—it's a lifestyle.

Keep reading to see the Rory Gilmore fashion moments that true fans will never forget!

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(Image credit: 2016 Warner Bros. Entertainment Inc. )

Rory wore this sweet floral dress for the night Logan met her grandparents.

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(Image credit: 2016 Warner Bros. Entertainment Inc. )

The Chilton uniform, of course. 

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(Image credit: 2016 Warner Bros. Entertainment Inc. )

How could you forget the dress Rory wore to prom with her then-boyfriend, Dean?

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(Image credit: Everette Collection)

Shenanigans with Lorelai typically looked something like this. 

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(Image credit: 2016 Warner Bros. Entertainment Inc. )

When Jess tells Rory he wrote a book and couldn't have done it without her (swoon), she wore this chic jacket. 

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(Image credit: 2016 Warner Bros. Entertainment Inc. )

Golfing with Grandpa. 

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(Image credit: 2016 Warner Bros. Entertainment Inc. )

The annual Stars Hallow dance marathon required a festive dress like this. 

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Lauren Eggertsen
Editorial Director

"Copy (200 words): Lauren Eggertsen is currently the editorial director of Who What Where and has worked at the company for nearly seven years, where she started as an associate editor and has since worked her way up. Lauren has over 10 years of experience in the fashion editorial space, starting her career with internships at Marc Jacobs, Marie Claire, and The Zoe Report, where she was later hired as their editorial assistant. Lauren has worked in the Los Angeles and New York Who What Wear offices but currently calls L.A. home. It is here where she leads and manages Who What Wear's fashion team and oversees all day-to-day editorial content and large tentpole moments. This includes all of the runway, trend, and shopping-driven content that ultimately helps to build a strong brand reputation within the industry. Lauren's role also includes helping to set the fashion direction for all original photo shoots and often styles many of the celebrity cover shoots, including big names like Sydney Sweeney, Lindsay Lohan, and Megan Fox. 


She has also attended multiple fashion weeks, including New York, London, and Milan, where her personal style has been featured on sites such as Elle.com, HarpersBazaar.com, and Vogue.co.uk. She prides herself on discovering and supporting small brands and on her knack for a good vintage shopping find. When she isn't working, she enjoys researching and dining at reputable restaurants around both her neighborhood and the globe.