Move Over, Rory: I'm Dressing Like Lorelai Gilmore This Fall

We may earn commission from links on this page, but we only recommend products we love. Promise.Courtesy of Ruby Ford-DunkerI first binged Gilmore Girls with my mom in 2016—a full 16 years after the show premiered. I related to the show's best-friend-like mother-daughter bond, found familiarity in the storyline, and it quickly became my comfort show. I even saw myself in Rory: I was a straight-A high-school student dreaming of becoming a journalist, and I adopted her wardrobe—plaid skirts and all.But as I've gotten older, my style has evolved. I still adore the nostalgia of Rory's wardrobe, but I crave a more expressive version, gravitating more and more toward Lorelai's closet. Ten years ago, I saw it as too quirky-mom-coded for my taste, but now, it feels exactly like what I was missing. Her style is grown-up but still playful, which makes it feel modern in the era of whimsycore. At a point where I'm intentionally curating a self-assured sense of style, it couldn't be more applicable to my wardrobe. So, I hit play on "Where You Lead" and decided to dress like Lorelai Gilmore.Courtesy of Ruby Ford-DunkerWhile I didn't have a tube of Vicious Trollop (the iconic lipstick Lorelai shares with Emily Gilmore) lying around, I pulled out a slew of turtlenecks, leather jackets, boots, and flare-leg jeans reminiscent of Lorelai's on-screen wardrobe. I started with one of my favorite Lorelai looks: a sky-blue long-sleeve styled with a midi skirt, knee-high boots, and a matching headband that she wears to one of her Friday Night Dinners with her parents, a weekly obligation in exchange for Rory's tuition. The ensemble was more maximalist than my usual looks, with each piece vying for attention. It ignored trends in favor of personal style, much like Jenna Rink's wardrobe in 13 Going on 30 and Carrie Bradshaw's in Sex and the City. The look felt nostalgic and charming, calling on the early '00s and reminding me that getting dressed is about expression, not copy-and-pasting trends.Courtesy of Ruby Ford-DunkerThe next outfit was a button-up (a Lorelai staple, often with unexpected elements like ruffles and vibrant colors). My take was a pinstripe version with a peplum waist from Anthropologie and dark flare-leg jeans from Just Black Denim. To my surprise, I didn't feel like I was cosplaying Lorelai. I already enjoyed reaching for button-ups and tailored jeans, so it felt like an outfit I'd wear on the daily. The peplum was the surprising detail that bridged my everyday style with Lorelai's playful, off-beat signature wardrobe.I expected to love every outfit that followed, but a few of the looks didn't resonate. Not feeling like myself in some of Lorelai's outfits, though, is actually what made me question why I liked her style in the first place. A trucker jacket, turtleneck sweater, and jeans, inspired by one of Lorelai's many Stars Hollow festival outfits, looks cozy and effortless on her but felt a bit too rugged and casual for my taste. Another look I didn't love on myself was a merlot turtleneck (mine from Intimissimi) and leather jacket, a combination Lorelai wears to Rory's school. On me, it felt too sophisticated—almost stuffy. That's when I realized I wasn't just drawn to Lorelai's style because of aesthetics but because of what it embodies.Courtesy of Ruby Ford-DunkerLorelai is a fast-talking, coffee-drinking, quick-witted woman who knows who she is and what she likes—her outfits are just an extension of the confidence she has in herself. Every look is intrinsically her: knee-high boots with a more classic skirt because she always has a little edge. A pop of red because she can't help but stand out in a crowd. Lorelai doesn't dress to win anyone's approval or to fit in (like when she wears Juicy sweatpants and Emily has a lot to say); her rebellious nature gives her the courage to dress honestly. Gilmore Girls costume designer Brenda Maben has said Lorelai wasn't styled by what was trending, but by her quirky personality. I wasn't after Lorelai's exact looks (though they're still iconic), but the confidence it takes to be so unapologetically yourself that it spills into your style.Courtesy of Ruby Ford-DunkerWhat started as a way to channel a more evolved version of a beloved persona turned into the realization that I didn't have to dress like a carbon copy of Lorelai; I just had to borrow her willingness to dress like herself. Rory may have taught me to embrace an aesthetic, but Lorelai gave me permission to dress for exactly who I am.Ruby Ford-Dunker (McAuliffe) is a fashion and lifestyle journalist featured in Vogue, InStyle, Elle, Who What Wear, Marie Claire, Brides, the New York Post, Business Insider, and more. When she’s not reporting on her latest fashion obsession, she can be found listening to Taylor Swift, hunting for the best vanilla latte, playing with her cats, or smiling her way through a dance workout. Email Ruby at therubybrand@gmail.com, and keep up with her on Instagram @rubyymcauliffe and Substack via Style Note.