2. £220, Umit Benan, thecorner.com

Is it possible for men to dress for a night on the town without reaching for a rented tux or a novelty waistcoat? Yes, says the expert Adam Welch

In lieu of options, men's fashion has rules. And its contemporary followers like nothing better than geeking out about them all – and we have the nostalgic, Hardy Amies-esque cast of the past decade's resurgent dandyism to thank for this. That's all well and good but it leaves us in a bit of a tricky situation when it comes to dressing for parties, where you're supposed to, you know, have a bit of fun, as well as look good in a dinner jacket. Thankfully – call it modern progress – the fashion world, and men themselves, seem to be rising to the challenge in this area, with new, more versatile evening options proliferating this winter, and an increasing feeling of laissez-faire as regards the stuffy old tuxedo.

In one sense, the dogged nostalgia of recent runways (cf Prada's gawky rollnecks and suede jackets; Gucci's shearlings and pastels; Dries Van Noten's nods to David Bowie's heyday) has made it easier to inject a wry, louche feeling into partywear. Jeremy Langmead, editor-in-chief of men's e-tailer Mr Porter, says this season is all about "a nice hint of 1970s glamour", and recommends navy tuxedo jackets worn with a fitted polo neck (preferably cream) or dark jeans and patent shoes. "Navy is the smarter option this season," he says. "And it's more flattering than black if you're over 35."

However, if it must be black, then new eveningwear line Rake Lounge, designed by former Browns menswear buyer Clive Darby, has a more generous approach to the classics. "I think there are more and more people that would like to put their own style take on something rather than feeling they have to conform, wear a uniform," Darby says. "The whole concept of Rake is that everything is sold as separates, to be able to have a bit more fun and flexibility about how the garments are worn. The jacket has been cut in a way that the proportions still fit with a jean, it doesn't look like it's been taken from a suit that's been broken up." Jacket and jeans? Yes, hmm. But Darby, like Langmead, maintains this retro look can be done in style: "There's ways you can put jeans with a dinner jacket and make it more flippant and louche."

Of course, the vintage Michael Caine look isn't going to work for every event, and for party dressing, as Darby puts it, "the most important thing is to respect the occasion". For a dash of the unexpected at more formal events, it's best to use more subtle sartorial tricks, according to Luke Day, fashion director of men's magazine GQ Style and the man behind Gary Barlow's much-lauded wardrobe on this winter's X Factor. "I think the small details can make a look more interesting," he says. "A gorgeous pocket square, a Lanvin flower pin or a tiepin collar can make an ordinary suit look more dressed up." Duncan Campbell, editor of Acne Paper, is in agreement: "While I can't get behind the spinning novelty variety, a bow tie, pocket square or cheeky coloured sock can be a great way to brighten up your look." As far as tailoring is concerned, Day recommends a three-piece suit, as it "always feels grander". Garth Spencer, executive fashion director of 10 magazine, champions the waistcoat alone as an outsider option, especially during the holidays. "Even if I hate them, it's a great way of wearing tailoring and still looking smart without wearing a jacket," he says. "Also, they're great for keeping in the Christmas gut and give you room to move your arms for more eating."

Now, how much is too much? The jury is somewhat out here. "New Year's Eve comes but once a year so better to be overdressed than underdressed, surely," Campbell says. Gianluca Longo, fashion editor-at-large at ES magazine, says we can afford to be more adventurous, and recommends adding a pair of studded Louboutin slippers for a "rock'n'roll touch", or a bright red jacket from the Louis Vuitton runway, "especially if you want to be noticed". Day, meanwhile, notes that there's a flamboyant side to the winter runways, which he says were "awash with Lurex, velvet and evening suits". (Dolce & Gabbana supplied the most dazzling of these.) But ultimately, says Charlie Gilkes, one half of the duo behind London night spots Barts, Maggie's and Bunga Bunga (where party excesses include a fancy-dress box full of Eurovision-themed clothes, amid much cheerful silliness), a real party needs you to "wear what you feel comfortable in". And a party pooper? "Trying to make a statement and seek attention. Especially when it's not your own party." You have been warned.