For me, fall always inspires a wardrobe refresh. Maybe it's my annual Gilmore Girls rewatch, but Rory and Lorelai's mix of preppy and early-Y2K style still feels just as relevant today—and every year, I find myself wanting to recreate it. If you're not sure where to start, celebrity costume designer Mona May, the creative force behind Clueless, has some advice.
"The quintessential, most important thing about the preppy look to me is a tailored look," May says. "Classic pieces with a tailored silhouette [are] really important. It's not sloppy look, it's not oversized—it's very fitted." Think plaid or pleated skirts, fitted blazers and button-downs, chinos, loafers, riding boots, argyle prints, and sweater vests.
Below, I curated near-identical pieces from the series, like Rory's “Muumuu” sweater from the pilot, Lorelai's sleek turtlenecks, fall coats inspired by the iconic Thanksgiving episode, and more.
Rory's cozy sweater outfits
Despite seven whole seasons and a spinoff series, one of Rory's most memorable outfits happens to be in the first few scenes of the pilot. And this is one look that is exceptionally and intentionally slouchy—but paired with classic denim and simple accessories, it still feels polished rather than oversized for the sake of it.
I have a near-identical version from Aelfric Eden, and it’s as cozy as it looks onscreen. You can read more about my thoughts and how to style it like Rory does in my review. We also found similar Rory sweaters, below.
Lorelai's iconic fall brown ensemble
The pumpkins in the background aside, Lorelai's outfit is peak fall. Her sleek, sophisticated style is a true time capsule of the early aughts, and with chocolate brown being a trending color for fall, this outfit certainly holds up.
Lorelai's turtleneck looks
If you watch the entire series, you'll notice that Lorelai sports turtlenecks a lot—even sleeveless ones, which merge her business casual attire with a timeless transitional silhouette. However, rather than chunky cable knit styles and oversized fits, she’s often seen in more refined, form-fitting options.
Lorelai and Rory's fall coats
Looking for a dressier cold-weather coat? Rory and Lorelai's peacoats from the "A Deep-Fried Korean Thanksgiving" episode in season 3 are so timeless and elevated. But, we also love the effortless flair of Lorelai's and Rory’s denim and barn jacket collection. For a pop of color, who can forget her iconic pink trench coat that transforms a white shirt and jeans into something glamorous?
Rory's preppy academic style
Attending prep school comes with a built-in dress code, but you can take cues from her uniform for a sporty prep look. Rory’s style at Yale is also influenced by her Chilton wardrobe, but ages with her for a modern preppy look that fits her maturity.
Lorelai's playful colors
Lorelai’s style is also rooted in classic prep, but she gives it a rebellious, modern update—a reflection of her complicated relationship with her parents and upper-crust New England society. She often incorporates preppy staples, like the layered white button-down pictured here, then adds playful pops of color, pattern, and texture for a distinctly early-2000s feel.
Emily’s tweed jackets and matching knits
We can’t forget about the queen of taste and classic style, Emily Gilmore. With every re-watch, I’m paying closer attention to Emily’s upper crust country club style—from her St. John matching knit sets to her Chanel-inspired tweed jackets.
The best part? You can merge Emily’s polished pieces with Lorelai’s early aughts styling for a more modernized look. Think: pairing a tweed cropped jacket with jeans or a knit skirt with a mockneck tank.
Rory & Lorelai’s graphic T-shirts
Throughout the series, Rory and Lorelai sport plenty of interesting graphic T-shirts that really showcase their personalities. But two are very memorable 26 years later: Lorelai’s bright pink tie-dye shirt that made quite the impression at Chilton and Rory’s “Reading is Sexy” t-shirt that is a newfound staple for #BookTok.
