Three Classic Films To Inspire Your Fall Wardrobe

Whenever I’m feeling stylistically challenged, there’s one place I turn to again and again for inspiration: Film.

I’ve always been intrigued by costume design and can sit through even the most awful movie as long as the clothes are interesting. It’s fascinating to me how fashion can help define a character, the arc of a story, or punctuate a conflict. Our clothes really do say so much about us.

Each season there are certain films I find myself repeatedly coming back to for outfit ideas, and with fall weather quickly approaching I’m sharing a few of my autumn favorites with you today. Check them out below, and be sure to click through to grab an inspired look of your own.

Love Story (1970): Ali McGraw’s wardrobe in Love Story is pretty much perfect, and one I find myself referencing again and again. It’s just so New England in the fall. Set — appropriately — in Boston, Love Story is considered by many to be one of the most romantic films of all time.

Starring Ali McGraw and Ryan O’Neal as two students who meet in college and fall in love, it’s McGraw’s wardrobe and natural beauty that really steals the show. Classic camel coats, collegiate sweatshirts, and cozy knits take center stage. Set against the backdrop of fall, it’s hard not to be tempted to copy each and every look.

Take a note from McGraw’s character, Jennifer, and throw an oversize jacket over a cable knit sweater and short corduroy skirt and add cold weather accessories, like a red beanie and go-with-everything boots.

Get the look: Miss Molly Textured Overcoat, Good Day Sunshine Mini, Following Directions Zipper Cape, Charlie Cuff Beanie, Detroit Ankle Boot.

Annie Hall (1977): If you haven’t already seen Annie Hall, go out and watch it, if anything just to see Diane Keaton’s incredible menswear-inspired wardrobe. I’ll admit to not being a huge fan of Woody Allen, but I make an exception for this film, which has been inspiring designers and stylists since it’s debut in ’77.

Set against the backdrop of New York, Keaton’s Annie is a comfortable and relaxed contrast to what we’ve come to know as iconic ’70s fashion. Cop her look with menswear separates, like these relaxed olive pants, button-up top and borrowed-from-your-boyfriend jacket.

Get the look: Cool & Clean Harem Pant, Cotton Boyfriend Shirt, Slouchy Boyfriend Jacket, Inter Weave Rogue, Faye High Crown Hat.

When Harry Met Sally (1989): Many people are quick to write off the ’80s as a stylistic disaster, but I disagree. Take the time to look past the shoulder pads and hairspray, and you’ll see an era of laid back, slightly preppy tomboy style. Meg Ryan’s character in When Harry Met Sally is a perfect example.

With NYC again as the backdrop to a love story (I swear I watch other movies), When Harry Met Sally focuses on the relationship between Sally, played by Ryan, and Harry, played by Billy Crystal, and asks the question: “Can men and women be friends?”

Sally’s wardrobe is, I’ll admit, iconically ’80s, but offers plenty of wardrobe inspiration nonetheless. Translate her mom jeans and blazer to relaxed boyfriend jeans and an unstructured jacket, and you’ve got the perfect weekend outfit for strolling through Central Park (or just down main street).

Get the look: Slouchy Textured Wool Coat, We The Free Sunset Park Thermal, Low Rise Relaxed Skinny, Vintage Canvas Ox Chucks, Ashton Plaid and Suede Baseball Hat.