classic films to inspire your autumn wardrobe


art: lillie leasure

Leaves are beginning to change colors. The breeze is shifting to make the hairs on your arms stand up. There are new menu items at your favorite coffee shops to welcome in the new season, and you have just begun bringing out your chunky sweaters and boots. With each new season comes fresh trends and a newfound excitement about getting dressed in the morning. 


This past summer, the “Coastal Grandmother” aesthetic ruled the season. If Diane Keaton wore it in a Nancy Meyers movie, it was sure to be in our wardrobes. Neutrals and blues, girly accessories and an abundance of linen and cotton pajama sets are some of the markers of the coastal grandmother aesthetic. 


We have not seen the last of the coastal grandmother, but the color palette is deepening and layering is coming back in full swing. There is still a focus on comfort, class and elevated basics that was at the forefront of coastal grandmother but with a warm spin for the fall weather. This fall is all about being the intellectual cool girl who lives in the city while her grandmother has retired to the peaceful coast of Nantucket. What better way to gain inspiration than to cozy up on the couch with a cup of apple cider and a cable knit blanket and flip on the television to your favorite fall movies? 


“When Harry Met Sally”

“When Harry Met Sally” is a quintessential movie for embodying Meg Ryan fall. The film follows characters Sally Albright (Meg Ryan) and Harry Burns (Billy Crystal) as they argue whether men and women can ever be just friends. The two travel from Chicago to New York to begin their lives separately, and the movie follows their trials and tribulations with finding love, but always brings the two back together whether they like it or not. The fashion of this screenplay is what makes it such a warm, fall film. Both characters bring equally exceptional fashion sense to the table with cable knit sweaters, dad jeans and turtlenecks. Many trips to the thrift store will make your wardrobe gleam with all these vintage essentials. 


“Dead Poets Society”

The first time you saw “Dead Poets Society” was, most likely, in a high school English class. If you did not fall in love with the film then, I beg you to give it another chance. Dark academia is the only way to describe the feelings of the classic film. Mystery, ancient tradition and nobility fill the movie with autumn nostalgia. What is possibly most memorable about the film is the fashion. In the weirdest way, it makes so much sense that the best fashion comes from ‘80s all-boys preparatory school students. Loafers, oversized glasses, crew neck sweaters and button-downs are all classics in your wardrobe that will never go out of style. As The Cut puts it, if “O Captain! My Captain!” wears it, you should too. 


“Autumn in New York”

Winona Ryder and Richard Gere play an unlikely couple in “Autumn in New York.” While the plot of the movie is profound, the excellent fashion is often overlooked. Glamour and class are unmatched with multiple different gowns and going-out attire. Charlotte (Winona Ryder) brings an eccentric touch to all of her looks with beautiful headpieces and her signature pixie cut. If you are willing to shed a tear for good fashion, “Autumn in New York” is of the best caliber. 


“Annie Hall”

This season is not completely rid of Diane Keaton’s fashion influence. We are jumping a little further back to young 1977 Keaton with her performance in Woody Allen’s “Annie Hall.” This disheveled romance film is filled with the charm Allen’s direction has come to be recognized by. Tweed blazers, neckties and oversized chinos are all caveats of the laid-back preppiness exuded from the characters. Keaton’s character Annie rotates through many ensembles of what was, until the ‘70s, considered men’s fashion. Annie and central character Alvy, played by Woody Allen himself, are even seen wearing the same wool blazer in different scenes of the movie, furthering the gender neutrality of their wardrobes. 


“You’ve Got Mail”

Another classic Meg Ryan film, “You’ve Got Mail,” brings a small-town feel to the big apple. Local boutique bookstore owner Kathleen Kelly (Meg Ryan) fights with a corporate blockbuster publishing house run by Joe Fox (Tom Hanks) to stay afloat. In this endeavor, the two fall for eachother in the most unlikely of ways. What is even more classic than the plot is the fashion. Layered knit dresses, button-ups with pencil skirts and oversized belted trousers are all brought together by costume designer Albert Wolsky. Wolsky is responsible for bringing us all of the perfectly curated looks that could fill our Pinterest boards forever.  


“Notting Hill”

Moving away from the multitude of films based around New York City, we’re traveling to London for the classic romance between William Thacker (Hugh Grant) and Anna Scott (Julia Roberts) in “Notting Hill.” What makes this movie so special is the director’s ability to make a film equally filled with meaning as well as humor. According to Vogue, outside of the fact that “Anna Scott stands in front of Will Thacker asking him to love her wearing a pair of flip flops, Julia Roberts’ character nails the lo-fi ’90s style that is enjoying a comeback.” Roberts sported the model-off-duty look before it was even a trend. Vans, leather jackets and berets are all you need to complete the Anna Scott look. Contrasted with William Thacker’s ‘90s preppy style, “Notting Hill” is filled with characters brimming with fashion sense. 


“A Rainy Day in New York”

Nothing quite matches waking up to gray skies and rain pattering on your window in the fall time. “A Rainy Day in New York” is that feeling bottled up in an hour-and-a-half movie directed by Woody Allen. Released in 2019, this is the most recent movie to come out on this list. It has all the same feels as the classics but with a modern-day twist. The star studded-cast of Timothée Chalamet, Dakota Fanning and Selena Gomez make their way through – you guessed it – a rainy day in the city. This movie proves there is nothing wrong with basing your outfit around the color of your umbrella. Get out your trench coats, plaid button-downs and denim to soak up the rain. 


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Hi, I’m Catie Pusateri, the Editor-in-Chief of A Magazine. My staff and I are committed to bringing you the most important and entertaining news from the realms of fashion, beauty and culture. We are full-time students and hard-working journalists. While we receive support from the student media fee and earned revenue such as advertising, both of those continue to decline. Your generous gift of any amount will help enhance our student experience as we grow into working professionals. Please go here to donate to A Magazine.