“Twenty-five years ago, a show called ‘Gilmore Girls‘ premiered and, apparently, took the season of fall hostage,” quipped “Gilmore Girls” alum Lauren Graham, joined by former costar Alexis Bledel, at the 77th Primetime Emmy Awards on Sept. 14.

Two-and-a-half decades after the show debuted, the mother-daughter coming-of-age series remains synonymous with autumnal coziness and Y2K fashion. To commemorate the series’ anniversary, WWD spoke with stylist Jasmine Caccamo, who works with Olympic gold medalist and soccer player Alex Morgan, about how the series’ fashion and style sensibility endures all these years later.

Airing from 2000 to 2007, “Gilmore Girls” coincided with the height of Y2K fashion trends — “it shows early-2000s style the way people actually wore it,” Caccamo told WWD via email.

“Lorelai brings the playful graphic Ts, wrap tops, low-rise bootcuts and tiny shoulder bags. Rory infused more of the ‘academic core.’ For instance…cardigans, pleated skirts, denim jackets and the classic Converse,” Caccamo said. Even the Gilmore family matriarch Emily, played by Kelly Bishop, showcased her own variation on style and trends.

“Emily is the polished anchor where we see more of the matching tweed sets, pearls, silk blouses. Together, you get the real Y2K mix of flares and fitted knits, suede and corduroy, a little kitsch next to quiet classics. It’s lived-in, not costume, which is why it still lands today.”

Caccamo describes each character’s wardrobe essentials in such terms that can still translate to 2025. For Lorelai, her style centered on “playful power: fitted wrap dresses, moto/leather, denim, boots, color and prints. She can do ‘budget meeting at 10, movie night at 7’ in one outfit.”

Rory provides a preppy foil to Lorelai’s Y2K looks with her “academic ease: cardigans, pleats, soft knits, simple denim, sneakers. At Yale she levels up, cleaner lines, sharper coats without losing comfort.” And Emily represents “curated classic: impeccable tailoring, tweed, cashmere, pearls, structured bags. Precision is the point.”

Indeed, Y2K is written all over costume designers Caroline B. Marx (2000-2001), Robin Lewis West (2001-2003) and Brenda Maben’s (2003-2007) wardrobe choices for “Gilmore Girls.” But several of the series’ staple looks had timeless quality with an aughts edge. Lorelai’s low-rise jeans and flared boot cut with a T-shirt or tank top and layered denim jacket could translate to today’s trends and understated streetwear style.

Rory’s wardrobe, by contrast, slightly differentiated with demure minimalist staples, knit sweaters, turtlenecks and a more structured look. Throughout the series, too, audiences witnessed Rory’s transformation from preppy Chilton transfer to Ivy League graduate.

As such, the series served not only to emphasize those ubiquitous Y2K staples — low-rise jeans, knee-high boots — but also charted how those trends ebbed a flowed via accessories, chokers transitioning to draped scarves, and hair styles — lest we forget Rory’s bangs and her one-episode pink hair highlights.

Beyond it’s definitive aesthetic association with the early aughts, “Gilmore Girls” has been defined by its autumnal ambience. “Stars Hollow fall is a layering 101,” Caccamo said. “The camel or charcoal coats, cable knit sweaters and plaid everything to the corduroy, knee-high/Chelsea boots, and a sensible scarf.” Today, those looks can be updated “with a straight-leg jean and a structured mini bag and you’re 2025 ready. It still is the same formula, texture and warmth [plus] smart top layer.”

The enduring watchability of “Gilmore Girls” and impact the series had on Y2K style is a credit to the show’s continued accessibility. At its core, the show is a coming-of-age story centered on a mother and daughter in a nondescript small Connecticut town.

Navigating intergenerational relationships, friends and romances lent a timeless quality to the series that translated to the costuming. The show’s residual popularity on streaming services like Hulu and Netflix and its subsequent follow-up miniseries “Gilmore Girls: A Year in the Life” see longtime fans return for an annual rewatch each autumn.

Fast-forward 25 years after its premiere and “Gilmore Girls” Core is now trending on TikTok with outfits inspired by the series. Fitted turtlenecks, sheer tights with muted skirts, cardigans and a general cozy vibe layer throughout contemporary takes on the “Gilmore Girl” aesthetic.