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 these with ease and sophistication? Modern tailoring is the answer. And TOM FORD has a reliably luxe way to make a splash. This plush velvet suit offers not just a touch of texture, but a sense of exclusivity – no less because MR PORTER is the only place you’ll find it. If you’re looking for a sense of occasion while not being too formal about it, strike the right note with a simple T-shirt and a snappy pair of leather monk-strap shoes from Mr P. – the perfect combo should the dance floor 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 Bing Crosby about it.

This merry-making 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, such as 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 wide-leg wool ones from The Row. You don’t need to mess too much with your leather jacket itself – this cropped style by Enfants Riches Déprimés, constructed in Italy from a supple textured hide, takes an iconic cut and elevates it. Wear yours with a classic white shirt or T-shirt to complete the look.

A hectic set of engagements means 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. With its mesmerising embroidered floral motifs, a Kartik Research shirt is a sure-fire sartorial talking point. Made in India in a celebration of local cultural heritage, you’ll find it as part of our Consciously Crafted edit. This semi-sheer cotton-voile shirt is also light and airy – the perfect fit when you’re negotiating your way around a festive crowd.

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 Valentino Garavani penny loafers: effortless ways to add a classic touch.