Lessons on how to dress for the season, from Messrs Steve McQueen, Richard Gere and River Pheonix.

When it comes to movie-inspired style, summer classics are endlessly referenced – the Italian Riviera chic of The Talented Mr Ripley, Mr Alain Delon’s batik-print shirt in Plein Soleil, the azure polos and short-shorts in last year’s Call Me By Your Name. But which iconic performances should we look to for inspiration as the nights draw in, the leaves flutter earthwards, and autumn starts doing its misty, mellow-fruitfulness thing? We’ve been scouring our vast DVD trove in order to bring you five seasonally appropriate looks it would be hard not to, ahem, fall for.

We make no apologies for including the oft-cited Mr Steve McQueen in our autumnal round-up; while everyone rightly exalts his way with a Prince of Wales three-piece suit in the original Thomas Crown Affair, we think his good cop vs bad mob boss turn as lieutenant Frank Bullitt in Mr Peter Yates’ Oscar-winner is criminally underrated, as is his wardrobe. If you can drag your eyes away from the legendary Ford Mustang chase scene through San Francisco, feast them on Frank’s knitwear treasury, from the presidential-blue polo neck teamed with a grey herringbone-tweed blazer to the ebony polo neck and stone-coloured driving coat via the burgundy shawl-collar cardigan and button-down Oxford. This is all-business casual for autumn, in a “you work your side of the street and I’ll work mine” kind of way.

Autumn, and a gentleman’s fancy turns to… tailoring. Or, in Mr Tony Leung’s case in Mr Wong Kar-Wai’s slow-burn erotic masterpiece, it turns to Ms Maggie Cheung, his next-door neighbour (and the wife of his own wife’s lover) in 1960s Hong Kong. She floats ravishingly through the movie in a parade of figure-hugging, high-neck cheongsams, while Mr Leung matches her smoulder for smoulder in an array of slim-fitted Mad Men-style suits, skinny ties and pocket squares (seven years before the TV show would take the style global), aided and abetted by his enviable selection of mid-century furniture and Mr Nat King Cole crooning “Perhaps, Perhaps, Perhaps” in Spanish on the soundtrack. So sultry you could strike a match on it.

What’s the abiding memory for all who’ve seen Mr Paul Schrader’s cautionary tale of a narcissistic male escort? Is it the film noir-y plot of murders and frame-ups? Nope. Is it the soft-focus sex scenes, with Ms Lauren Hutton, among others? Nope again. It’s the sight of Mr Richard Gere, as the titular gigolo Julian Kaye, laying out his Armani wardrobe with a go-get-’em-tiger smirk while singing along to Smokey Robinson’s “The Love I Saw In You Was Just A Mirage” (you could try this at home) and doing a line of cocaine (erm, perhaps better not try this at home). The film established Armani as a major Hollywood player but, for autumnal purposes, we’d set aside the soft-construction suits and striped shirts in favour of the knitted polos, which we’d just bet are in the finest, most yielding weave of merino wool.

Mr Gus Van Sant’s downbeat study of street hustlers kick-started several things: the careers of Mr River Phoenix and Mr Keanu Reeves (the former’s tragically cut short by his early death), a grimy-but-dreamy US indie movie aesthetic, and grunge. The same year that Nirvana released Nevermind, its style template was all over Mr Van Sant’s characters, from the grey-marl hoodies to the plaid and denim jackets, untucked chambray shirts, beanies and shearling-trimmed coats. Not only did such layered, lived-in looks match the autumnal mood of the movie; they also went on to influence the haute-streetwear designs of everyone from Vetements to Off-White.

Where do we begin with Mr Arthur Hiller’s classic romance? It has everything an autumnal classic should – burnished New England fall foliage, Hallmark-card-worthy one-liners (“Love means never having to say you’re sorry”), and – spoiler alert! – a major protagonist succumbing photogenically to a terminal illness. The focus has always been on Ms Ali MacGraw’s hunker-down wardrobe – the woollen pea coats, ribbed sweaters and leather gloves – but for us, Mr Ryan O’Neal’s Wasp-y, white-shoe law firm attire – the herringbone-lined trench coats, the pastel pullovers, the Glen plaid sports jackets – define preppy back-to-school style just as eloquently.

The men featured in this story are not associated with and do not endorse MR PORTER or the products shown