The festive calendar brings some of the biggest nights out of the year. These are, in theory, the easiest to plan for sartorially. Occasions where the mantra of go big or go home applies. That said, they can also be unpredictable, nights where an intimate dinner can segue into drinks, then partying till the wee small hours.

Looking to navigate all of these with ease and sophistication? Modern tailoring is the answer. Swedish brand Saman Amel is a reliably luxe way to make a splash. The classic Italian craftsmanship of this wool and mohair blend suit jacket perfectly balanced with the contemporary silhouette of matching wide-leg trousers. You’re looking for a sense of occasion while not being too formal about it, so strike the right note with a simple white T-shirt and a snappy pair of leather monk-strap shoes from Mr P. – the perfect combo should the dancefloor beckon.

’Tis the season for knitwear. However, the temptation to don attention-seeking sweaters should be approached with due caution. Think causally dialled up knits instead, embracing the party spirit with say, a playful paisley patterned cardigan from Corridor that’s cosy without getting too Mr Bing Crosby about it.

This merry maker Jacquard knit is best paired with trousers that err on your more minimalist side, such as these pared-back chinos from Our Legacy. A couple more things: Canali’s fringed brogues bring both comfort and joy this festive season while fine jewellery from Spinelli Kilcollin, like this Sirius ring – hand-cast from polished 18-karat gold – is the perfect little festive treat to yourself.

Some festive events call for a more measured approach without going full humbug. The seasonal office party is a classic example; you’ll probably go from office to pub, so you’ll want to dress in a manner that befits both. It’s the date in the festive diary you should approach with the kind of smarts that got you the job in the first place.

So, start from the ground up, with a pair of classic penny loafers from ZEGNA, which will mark you out as a someone who puts thought into things. Then consider quietly statement trousers, such as these wool-flannel pair from Auralee. Keeping things close to business-as-usual, but with some sense of occasion is the key here – a Mr P. leather jacket is relaxed and sleek, while a luxe take on the classic T-shirt suggests you’ve made a special effort for the team.

A hectic set of engagements mean even the most gregarious among us can find our social battery drained by mid-December and finding fresh topics of conversation can become as arduous as present wrapping. This is where statement shirts come into their own. A Kartik Research shirt, with its mesmerising embroidered floral motifs, is a sure fire sartorial talking point. Crafted in India in a celebration of local cultural heritage, this semi-sheer cotton-voile shirt is also light and airy – the perfect fit when you’re negotiating your way around a crowded festive social.

When dressing for party season, pay attention to the details: a piece of fine jewellery like a bracelet from cult favourite M. Cohen by MAOR is a charming way to elevate a look. Then think classic: balance out the statement pieces with low-key tailoring, such as a pair of UMIT BENAN B+ tailored trousers and Manolo Blahnik penny loafers, effortless ways to add a classic touch.