STREAMING GUIDE

8 Perfect Fall Movies That Double As Autumn Style Inspiration

WHEN HARRY MET SALLY..., (aka QUAND HARRY RENCONTRE SALLY...), front from left: Meg ryan, Billy Crys
©Columbia Pictures/Courtesy Everett Collection

After a dreadful bout of intense late summer heat, we can finally utter the words “sweater weather” and have the phrase be a truthful description of the vibe on the East Coast. Almost nothing feels better than just fully leaning into being basic in the fall, and that includes bundling up, sipping a warm beverage, and staying inside to watch movies because what else are you going to do with your weekend once you’ve kicked around the (few) crunchy leaves that have fallen to the ground and finished your apple picking escapades? So, here in this collection that should tide you over until Halloween, are eight classic fall movies that are autumnal in spirit and dare we say a good source of fall fashion inspiration (you have to admit that both The Fantastic Mr. Fox and When Harry Met Sally rank pretty high on the tweed and corduroy index).

1
You’ve Got Mail (1998)

Why you want to watch it this fall: It’s been over 20 years since Nora Ephron‘s prescient romantic comedy You’ve Got Mail premiered, and it captures a New York that just doesn’t exist anymore. “Don’t you love New York in the fall?” is such a basic, rhetorical question uttered by Tom Hanks as Joe Fox, the heir to a big box bookstore threatening to put Kathleen Kelly’s (Meg Ryan) little bookshop out of business, but hey, he has a point. Where to watch it: Amazon Prime

2
Fantastic Mr. Fox (2009)

Why you want to watch it this fall: The titular character in Wes Anderson’s Fantastic Mr. Fox may be animated but he still kills it in a corduroy jacket. Where to watch it: Amazon Prime

3
Dead Poets Society (1989)

Why you want to watch it this fall: Yes, back to school season is technically in September, and the all boys school academic chic look works for all seasons, but it’s also just always a good time to watch the young men of the Dead Poets Society learn the true meaning behind a Walt Whitman poem. Where to watch it: YouTube

4
Good Will Hunting (1997)

Why you want to watch it this fall: The best season to hear Matt Damon ask, “How you like them apples?” is indeed during apple picking season. And though it might be painful to admit, Ben Affleck gets a few ’90s fall fits in this classic, too. Where to watch it: Amazon Prime

5
Love Story (1970)

Why you want to watch it this fall: When else are you supposed to watch the rom-com that set the standard for all future rom-coms after its 1970 debut besides the cozy seasons? Where to watch it: Amazon Prime

6
October Sky (1999)

Why you want to watch it this fall: Well, the title says it all really, but Jake Gyllenhaal’s flannel wardrobe speaks volumes, too. Where to watch it: Hulu or HBO

7
When Harry Met Sally (1989)

Why you want to watch it this fall: Sally’s blazer game and Harry’s sweaters are so evocative of the decade from which this film was born, but really work in 2019, too. Where to watch it: Hulu or HBO

8
Autumn in New York (2000)

Why you want to watch it this fall: When else are you supposed to watch a movie titled Autumn in New York besides autumn, and hopefully also while you’re in New York? Where to watch it: Amazon Prime