With autumn’s onset in full swing, it is officially the “fall must-watch” season, and you already know the lineup. We all know what happened when Harry and Sally met, we grew up with Lorelai and Rory, and we swooned (and screamed!) for Blair and Chuck. Their stories have characterized the season for decades, but what about their wardrobes? Let’s consider whether their fashion choices are just as enduring.
Sally’s high-waisted trousers, yellow button-down, and navy cardigan practically scream late-80s. Her style is certainly famed for its association with Central Park’s orange fall foliage, but let’s be honest: the hair is the real star. The voluminous blow-out and middle-parted curtain bangs could be a copy-and-paste advertisement for your favorite haircare brand, and her layered “lob” is still a blueprint for women everywhere looking for a seasonally appropriate cut.
It’s impossible to discuss Sally without giving Harry some credit. His flannel button-down and boyfriend-cut Levi’s are the pinnacle of late-80s men’s styling, and his white Reeboks seal the deal. Nowadays, it’s rare to see men’s fashion leaning into the “boy-next-door” look, so there’s something incredibly charming about the simplicity of Harry’s look. Harry didn't dress to make a statement; he dressed for himself, and that is timeless.
Rory is no stranger to the long-sleeve sweater, a choice perfectly fitting the crisp fall weather customary to her hometown of Stars Hollow, CT. More muted in color, this look reflects Rory’s growth and maturity from teenage girl to young woman. Her knit navy mock neck and dark plaid skirt layered over tights are nothing if not characteristic of autumn. Add her dark fold-over purse, and it’s almost difficult not to envision her on a college campus… maybe even at Georgetown.
Lorelai and Rory are nothing if not complementary, acting as matching puzzle pieces that complete one another. Even if their personalities don’t always align, there’s no doubt they stole outfit inspiration from one another. Lorelai, the mother of the midi skirt, pairs burnt orange with black and burgundy – the colors of each piece complementing one another in a perfect arrangement of fall coordination. Rory’s outfit is quintessential early 2000s but would blend in effortlessly today, and her olive-green cable-knit sweater and sheer tights tie the timelessly autumnal look together.
When she isn’t stunning viewers with her speedy humor and pop-culture wit, Lorelai has no trouble reminding everyone that she’s a businesswoman. Her tailored skirt suit and black pumps (and coffee in hand, of course) are strikingly different from her characteristic baby-tee but are a natural fit, nonetheless. Chic? Definitely. Timeless? No question. Professionally polished and fashion-forward? Consider it MASH approved.
It’s difficult to discuss fashion and Gilmore Girls without mentioning our French fashionista, Michel Gerard. Having attempted several times to pass off his custom-tailored suits as business expenses, Michel knows how to dress. There’s something comforting about the season of fall as pattern-consistent: plaid and neutrals return from the back of the closet, leaves turn orange and fall from the trees, and our television favorites revisit our screens. There’s a quiet comfort in this consistency, and Michel’s style is no exception. The variation in his fashion comes not from flashy excess, but rather from classy commitment to a style silhouette. Sharp tailoring, rich fabrics, and pieces made to last: like autumn itself, Michel’s style is something we can always count on.
Blair Waldorf: our designer daughter who never fails to stun in autumnal fashion. Her taste is elegant and overstated, and her ability to match seemingly clashing patterns and styles is, in one word, iconic. In this look, her muted beige cape sits over a glittery gold mini dress, finished with sheer black lace tights and black kitten heels. Her style is so uniquely “Blair,” guided by personal taste rather than by trend, and a signature never goes out of style.
If anything is timeless, it’s well-tailored fashion. While the matching headband might be a sign of the times, Blair’s satin plum mini dress is certainly fashionable beyond the early-2000s. And though we’ve seen a resurgence in fashion styles owned by that era – think low-rise, thrifted apparel – Blair’s lookbook is inspired by an admiration for luxury designers and Vogue editorial looks. The deep purple exudes fall, and we’re seeing a resurgence in headbands that Blair certainly wouldn’t argue with. With a fashion designer for a mother, it’s a birthright that Blair be endowed with so many amazing looks.
Here, the delicate, hyper-feminine white pointelle mini dress, cinched at the waist with a white bow, is countered by her black lace tights and black tulle headband. It’s a cinematic parallel to her personality: capable of being sweet, sincere, and delicate but undoubtedly cunning. Though it fits the season perfectly, Blair’s outfit speaks to more than just fall, emphasizing duality and transition. We see white pointelle as a summer staple, but Blair demonstrates that, styled correctly, transitional pieces can be showstopping in any season.
Gossip Girl fashion cannot be comprehensively analyzed without properly paying tribute to the school uniforms turned runway fashion. Blair and Serena took on the task of personalizing their private school uniforms in their own ways, but Serena’s speaks to her wild and free nature. From her casual cardigan to her over-the-knee socks, Serena’s personality infuses every styling choice. Gossip Girl is regarded as a fall TV classic for this very reason: the idolization of the school season in New York City augmented by spectacularly unique fashion choices.
There are few New Yorkers who can compete with Serena and Blair when it comes to recognizable personal style, but Chuck Bass is one of them. The chocolate brown stripes that run the length of his perfectly tailored suit are difficult to imagine on anyone else. Looking ready to stroll through Central Park, orange leaves falling overhead, Chuck exudes a strong sense of self and confidence that speaks to independence from influence. This conviction is admirable, and it remains well-demonstrated through his style: custom suits and luxurious taste that adhere to the authentic image of Chuck Bass, our king of fall fashion.
With autumn in full swing, it’s the perfect occasion to dissect how the fashion industry plays on changes in the weather, in trends, and in personal discovery. If fashion and style are how we arm ourselves in the world and communicate how we want to be perceived, it can be revealing to dissect how those styles vary when the seasons change. Transition is human, as natural as the leaves falling in October, and the fashion industry hinges on the cycle of human growth and style rebirth alongside the changing of the seasons.
At a time of year when we roll out our coats and dust off our boots, many begin to prepare for the cozy season, surrounded by friends and family, embracing loved ones and diving into human connection. Fashion mirrors society, and as we move into the colder months, brands are quick to meet our craving for warmth, comfort, and familiarity.
