The ultimate list of guilty-pleasure holiday movies – and how to create the nostaglic looks.

It’s December, which traditionally means pouring a glass of something fortified, settling down with the family in front of the TV and watching a Christmas film. But what makes a good one? A festive subject matter is a good place to start. If Santa and his reindeers don’t make an appearance, that’s fine, but the plot of the film ought to at least take place around the Christmas period. A story that reinforces one of the moral lessons of the festive season is crucial, too: love triumphing over hate, optimism getting the better of cynicism, good people getting what they deserve, and so on and so forth.

When it comes down to it, though, what a good Christmas movie should really do is take you back. Nostalgia is the lifeblood of the festive season. For a few short days, the past mingles with the present and we fall back in step with tradition. It’s a time for revisiting old stomping grounds, listening to old songs and drinking with old friends. It’s a time for looking back on the way things were. It follows, then, that a good Christmas film doesn’t actually need to be a good film. It just needs to be one that you’ve watched before.

If you’re struggling for inspiration this festive season, try one of the following eight classic Christmas films on for size. And we’ve told you precisely what you need to wear while you watch them.

Christmas. According to Mr Andy Williams, it’s the most wonderful time of the year. And it is, if you’re a child. For adults, though, the idea of greeting Christmas with wonder is… well, it’s absurd. And that’s exactly what makes Elf so brilliant. The infectious enthusiasm of Mr Will Ferrell’s character, Buddy, a fully grown man who grew up at the North Pole and is convinced that he’s an elf, reminds us of how we all used to feel during the festive season. A movie to melt the cold, cynical heart of even the most committed Scrooge, Elf has rightly earned its reputation as a Christmas classic, and while it’s a stretch to describe Buddy as a style icon, we can’t help but notice a similarity between his green felt coat and a few of this season’s shearling-lined worker jackets.

An ultra-violent home invasion thriller for kids, Home Alone was always destined for cult status. As an allegorical tale it’s highly questionable, promoting as it does the doling out of heavy-handed vigilante justice; the booby traps that eight-year-old Kevin McCallister sets in order to repel the hapless burglars Harry and Marv are just plain sadistic, and some look capable of inflicting serious harm. As a Christmas movie, though, it’s hard to fault. The colour palette is an uninterrupted sea of red and green, it features a feel-good orchestral score from Mr John Williams, and most importantly, it reinforces the core message of the festive season, which is that family comes first – and it’s OK to kill anyone that doesn’t agree. (We’re just kidding. Murder is never OK.) First released 27 years ago, Home Alone is finally being recognised for its contribution to the world of men’s style, too. To achieve the “Kevin McCallister look”, you’ll need a woollen bobble hat, plenty of playful knit patterns and a good khaki duffle coat or bomber jacket. Staple gun optional.

This 1983 cult classic from director Mr John Landis uses the holiday season as a backdrop, rather than a central plot device. But don’t let that fool you into thinking that it isn’t a Christmas movie; it is, and a great one at that. Trading Places tells the story of two ageing stock brokerage owners who make a vulgar bet with one another. Given enough money and opportunity, could any lowly scoundrel make a success of himself? Moreover, faced with financial adversity, would any high-flyer see his life fall into ruin? In order to settle their wager, they frame their most successful broker (Mr Dan Ackroyd) while simultaneously elevating a street hustler (Mr Eddie Murphy) into his old position. A heartfelt morality tale that nods to Mr Charles Dickens, Trading Places might just be the best alternative Christmas movie ever made, and, thanks to its setting in the financial district of 1980s Philadelphia, it has the added benefit of being packed with great examples of sharp-shouldered, retro power dressing. One caveat: the clothes aren’t the only things from the 1980s. There are some seriously outdated jokes, too.

The third cinematic instalment in National Lampoon’s Vacation series offers up comforting festive tropes aplenty. There’s the too-big Christmas tree, the power-draining lights display, the unexpected visit from the unsavoury relatives, the disastrous meal, the kidnapping, the Swat team... you’ll almost certainly relate to a few of them yourself. And if not, then there’s always the clothes. As Clark Griswold, Mr Chevy Chase offers up a picture-perfect study of the late 1980s suburban dad, his homely chunky-knit cardigan and pale blue shirt providing the backdrop to the novelty tie and – not seen here – Santa hat. It’s a look that we’ll be borrowing ourselves this Christmas as we manoeuvre our 14ft Norway spruce into position.

In this mid-2000s festive rom-com, two lovesick women from opposite sides of the Atlantic swap homes over the Christmas holidays. One, played by Ms Cameron Diaz, is a workaholic film trailer producer from Los Angeles who lives in a palace of minimalist luxury. The other, played by Ms Kate Winslet, is a journalist from London who lives in an impossibly quaint countryside cottage. They each fall in love, of course – one with a widowed single dad and the other with a charming, if not conventionally attractive, film-score composer. (Where do these Hollywood scriptwriters get their ideas?) On paper, The Holiday sounds awful. From a critical perspective, it is. A score of 47 per cent on Rotten Tomatoes is not the hallmark of a classic. But critical acclaim is not a prerequisite of a good Christmas movie, as we all know, and besides, there’s something about The Holiday that just charms the socks off us. Maybe it’s because it’s just over a decade old, making it prime nostalgia fodder. Maybe it’s Mr Jude Law’s overcoat and cashmere scarf tied just so. Who knows?

Is Willy Wonka & The Chocolate Factory a Christmas movie? This one caused a great deal of debate in the MR PORTER offices. It isn’t set at Christmas, so technically you’d have to say no. On the other hand, it is a mainstay of the festive TV schedule, and it does offer prolonged screen time to two things without which Christmas morning would arguably be incomplete: chocolate and pyjamas. The bedridden (until he claps eyes on a bar of chocolate, anyway) Grandpa Joe spends the first half of the movie in a modish night shirt, while Charlie Bucket opts for a standard pyjama set, which he switches out for a chic navy rollneck and flares before making his fateful trip to Willy Wonka’s factory. When it was released in 1971, the costume direction was presumably intended to emphasise the impoverished circumstances of Charlie's upbringing. Four decades later, he just looks cool as hell. That’s fashion for you.

It’s A Wonderful Life follows the story of George Bailey, a suicidal man whose bid to end his own life is interrupted by Clarence Odbody, a guardian angel who shows George what life in his hometown of Bedford Falls would have been like had he never been born. Despite the dark subject matter, this is perhaps the quintessential feel-good Christmas film, and at more than seven decades old it still feels remarkably fresh – a testament to the timelessness of the Christmas message that underpins the story. And while you might not find it particularly aspirational to dress like a man on the brink of suicide, our protagonist has some serious style, too. We’re particularly enamoured of his collegiate tie and herringbone tweed overcoat.

When it was released in 2001, Bridget Jones’s Diary didn’t just do wonders for the self-esteem of heavy-drinking single women in their thirties; it also significantly boosted the profile of the now-iconic ugly Christmas sweater. At the moment when Bridget and the audience first clap eyes on Mr Colin Firth’s stuffy human rights lawyer, Mark Darcy, he is dressed in a dark green sweater with an enormous reindeer design on the front. Our protagonist is not impressed, her internal monologue expressing her disappointment as he turns around to reveal the sweater in all its glory: “Maybe this was the mysterious Mr Right I’ve been waiting my whole life to meet? Maybe… not.” Oh, Bridget. If only you knew how fashionable the garish festive sweater would become. From Gucci to Thom Browne, every major superbrand under the sun now includes some variant on the intarsia-knit graphic sweater in their fall collections. Mark Darcy, style setter? You heard it here first.

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