A film we go back to time and time again for the utterly chic wardrobe of Jennifer (the Oscar winning character portrayed by Ali MacGraw), who is in possession of some of the best coats out there. The surprise hits are the stripy Harvard scarves and an impossibly elegant red dress. Be prepared to cry over more than just her fabulous wardrobe, though. If you’re only here for the outfits, you can always cheat and cut the film short before the waterworks set in.

When Harry Met Sally, 1989
Sleepless in Seattle, 1993
You’ve Got Mail, 1998

These films offer up some of our most commonly used film quotes:
“You’re right, you’re right, I know you’re right.”
“That caviar’s a garnish!”
“Quelle Nightmare”
“Waiter! There’s too much pepper on my paprikash!”
“Patricia makes coffee nervous.”

Who needs The Godfather when we have Nora and her magnificent scripts? When Harry Met Sally, Sleepless in Seattle, and You’ve Got Mail are all incredible in their own ways. The through line is, of course, our beloved Meg Ryan, who always wears impeccable trousers. Our top picks are the tracksuit bottoms in Sleepless in Swattle, or her silky khaki numbers when visiting her brother, which later also appear in When Harry Met Sally, during the infamous scene at The Met. Finally You’ve Got Mail, where it’s a toss up between the iconic pyjamas at the start of the film, or the chinos she wears later on. This is all without mentioning the knitwear, or the incredibly cosy vibe these films give off. We often say that modern films are afraid of good dialogue, and Ephron’s films offer that in abundance. In the immortal words of the director, Rob Reiner’s mother, “I’ll have what she’s having…”.

These films kick off the Diane Keaton section of this piece, which you will have to forgive me for. She just is so chic and whenever she’s in a film, you can’t help but take note of her loafers, shirts and tailoring.

I have a fondness for the sequel as Keaton really dials up her shirting as her maternity wear, and it also includes the incredible styling of Frank and his baby workout. While these films are necessarily set exclusively during autumn, the lighting gives a certain golden hue of warmth that certainly makes you feel like it’s autumn. There’s also a feelgood factor to the screenplay that feels akin to snuggling up with your duvet on the sofa, a quality that we can attribute to the writing of Nancy Meyers, of course!

If, like some of the team here at TRS, you prefer to cosplay as an old British gentleman (namely my late Grandfather), then Annie Hall is for you. Waistcoats, ties, cords, tweed, knits – you name it, Diane Keaton wears it. It’s also a very beautiful film that balances comedy and touching honesty.

A very chic stylist once described her Autumn/Winter style as very “Robin Williams in Good Will Hunting” aka retro cardigans, cords and shirts. However, you can’t knock the looks from Matt Damon either – those workwear zip up jackets? Varsity jackets? We’re in.

We also have a soft spot for this film due to a combination of Robin Williams’s monologue and Matt Damon’s curtain bangs. Style aside, this is a very touching coming-of-age film about a young man trying to find his identity that we think everyone should see at least once.

A little known 80s classic from Nancy Meyers, Baby Boom follows a city slicker moving to snowy Vermont with her new baby, trying to make it work. Starting with classic 80s suits, Diane Keaton’s character then swaps to the ease of tailored trousers, knitwear and overcoats. Her Vermont farmhouse is pretty idyllic too, especially if you want to get yourself into the ‘wintery but not quite Christmas’ mood.

Okay, this one is a little off-topic, but you’ve got to have a period drama here to bring the ultimate in cosy vibes. The way the costumes were developed so that Jo (played by Saoirse Ronan) and Laurie’s (played by Timothee Chalamet) clothes could be shared between the two characters is one of our favourite details. And just wait for the scene on the hill…with the autumn leaves in the backdrop, golden hues of light, passionate dialogue and Laurie’s velvet waistcoat… I’m getting carried away just thinking about it! And this is before we’ve even talked about the warmth of the March home. This iteration of Little Women is a standout in every category (in our humble opinion).

If anyone has seen the BRATS documentary, but hasn’t seen St Elmo’s Fire, now is your time to rectify that. Just wait until you see the coats, the 80s styling, and a young Rob Lowe. Before there was Brat, there was the Brat Pack which features some of our favourite 80s actors in some of the best coming-of-age films we can think of.

Ally Sheedy’s character has a particularly nice dark green overcoat, so keep an eye out for that. Otherwise, be prepared for a swath of plaids, thick blazers, and fuzzy cardigans as we follow these Georgetown graduates through seasons of self-discovery and 80s fashion.

This instant classic will leave you wishing you could be abandoned for the Christmas holidays at an upstate NY school. The setting, the music, and the clothes all transport you to a place in time so evocative you can smell the dusty bookcases and mahogany wood. Nostalgia aside, The Holdovers is a beautifully poignant film with equal parts style and substance that will have you laughing, crying, and cringing. Discomfort and joy indeed.

Ok less about style (although these jammies are cute), but definitely an autumnal film to cosy up with; Fantastic Mr Fox is the best of Wes Anderson (we said what we said). A witty and stylish film that features rust coloured corduroys and preppy monochromatic two pieces (yes, we might be slightly jealous of the outfits of these fictional animals), Fantastic Mr Fox will have you wanting to sip warm cider, wearing striped pyjamas in your very own den…even the voices of George Clooney and Meryl make us feel calmer.