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.

Fall Film Fashion 13

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.

Fall Film Fashion Screen Cap 9

Fall Film Fashion Screen Cap 7

Fall Film Fashion 14

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.

Fall Film Fashion Screen Cap 6

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Fall Film Fashion 15

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 CoatWe The Free Sunset Park Thermal, Low Rise Relaxed SkinnyVintage Canvas Ox Chucks, Ashton Plaid and Suede Baseball Hat.

Fall Film Fashion Screen Cap 2

Fall Film Fashion Screen Cap 1

Do you have a favorite film for fashion inspiration? Please share!

More fashion and style posts from the BLDG 25 blog.

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9 years ago

So far this is my favorite feature you’ve done, Julie!! So creative and inspiring. When Harry Met Sally is also one of my favorites :)

9 years ago

Devil Wears Prada once Andie feels more at ease with herself and Amelie for French quirkiness!

9 years ago

I love this post! I totally agree with seeking outfit inspo from film – I love 80s cult classics like Pretty in Pink and Heathers!

9 years ago

True story: at some point when I was officially a “grown up” (whatever that means) my mom and I had a little stay-at-home date, watched Love Story, and totally admired damn near every outfit. Her fall style was perfect and I now want the perfect overcoat.

9 years ago

The Runaways was super style inspiring! Love this type of post. I say make it a feature!

9 years ago

Ooh I love the Love Story look. I’m thinking a printed skirt instead of corduroy but loving the rest of it! :D xx

Little Miss Katy | Fun, Food & Fashion!

9 years ago

I love love love this post, so inspiring! Annie Hall and When Harry Met Sally are two of my all-time favorite movies, and are styled just perfectly :)

Kassandra | The Desert Poppy

9 years ago

I love this post and the outfits you put together to match the movies. I think the last outfit in my favorite I’ve been on the lookout for the perfect mustard sweater.

9 years ago

Wow, this makes me want to go out and find all these pieces today. Thank you for this!

9 years ago

love this post! such great inspiration.

9 years ago

I love this – what a great idea for style inspiration. The job of a film stylist would be a dream – you leave behind so much evidence of an era! Amelie, Breakfast at Tiffany’s, episodes of Sex and the City… all so great.

Warm Regards,

9 years ago

I do a weekly series on fashion in film! These are some great recs!

9 years ago

Funny Face! I just watched it and was smitten with all of Audrey Hepburn’s looks–the black sweater with black cigarette pants and loafers, the tan raincoat, the white button down. Simple and classically stylish.

9 years ago

A Star is Born – Barbra Streisand has THE greatest wardrobe in that film. (And most of it was actually her own clothes.)

9 years ago

Oh too many to choose from! For 60’s chic, I can’t go past Factory Girl – Sienna Miller must have had a ball playing dress-ups Edie Sedgwick style!
For 70’s inspo I urge you all to check out Dazed and Confused if you have not already. As they say, bell bottoms, macramé and mood rings! Throw Almost Famous into the 70’s mix too as I long for every piece Kate Hudson got to wear in that flick!
80’s I’ll skip as I was there… ; )
Which leaves my beloved 90’s grunge – I recommend Mad Love with Drew Barrymore, for a playful, feminine take on the look that defined a generation. Oh how I love that yellow shirt! Throw in Singles, Reality Bites and Alyssa’s tomboy yet sexy take on the ol’ jeans and a tee in Chasing Amy and I am in heaven!
Long I know, but so much passion for this topic! ; )

9 years ago

I was just thinking, before I even read the post, that Annie Hall is great fall wardrobe inspiration. Also, the vintage French lovelines in La Vie en Rose <3

9 years ago

I love this post! I’m always inspired to cycle out my closet after I watch an 80’s or a 90’s movie. One movie that really gets me going is Heathers (1988) with Winona Ryder. The outfits are so rad. I’m definitely going to watch all of these movies and hopefully I’ll get inspiration too! Thanks!

9 years ago

This is such a great post! Are the jeans in the second outfit from Free People?

8 years ago

Magic post !
I’m in love really with the outfit inspired from Sally ! the coat seems sooo soft !

8 years ago

I love Audrey Horne’s style from Twin Peaks.

In films, I think Rachel Weisz’s wardrobe in Brothers Bloom is perfect and, of course, Margot Tenenbaum is stylish as hell!