A Comprehensive Guide To Dressing For The Party Season

Hugo Boss serves up four smart and sophisticated looks to see out the festivities in style

The festive party season should be a time of cheer. But with work, social and familial commitments often overlapping, the run-up to the big day is rarely the glittering succession of frivolities we imagine and can, instead, become something of a fraught affair. And nowhere is this more keenly felt than when it comes to the question of what to wear. 

Will wearing that tie to the office party raise a smile from your boss – or an eyebrow? How should you decode the “black tie, optional” dress code on that winter wedding invitation? And is a shawl or peak-lapelled tuxedo the better choice to impress your new clients? During the hectic holiday period, we’re more prone than ever to suffering from these sartorial anxieties.

So, to save you the hassle of trying to decide which shirt goes with what, we’ve put together a foolproof guide on how to get it right on the night – with the help of our friends at Hugo Boss, the German master of classic-meets-contemporary style.

The Office Party

Do not mistake the office party for a traditional party; no matter how close you perceive your relationship with your colleagues, there’s no such thing as truly letting loose with them or, more to the point, your boss. It may sound obvious, but don’t do anything you don’t want to be discussed at length come Monday morning (or, for that matter, still overhear faint chatters about in January). In summary, there are many ways the office holiday party can go wrong, but your outfit doesn’t have to be one of them. 

Unless the invitation clearly states it, you can assume that a full tuxedo isn’t necessary. That doesn’t mean you can’t make an effort, though. A suit is a pragmatic choice, whether or not it usually forms part of your workaday wardrobe; if it does, we suggest opting for a fabric, pattern or cut you wouldn’t typically go for. That way, you can’t be accused of simply showing up to the party in your work clothes.

This single-breasted puppytooth suit from Hugo Boss’ latest collection has a few features that set it apart from your Monday to Friday attire. There are the flush patch pockets, for one, and the trousers, which are fitted with a hidden drawstring waistband for a little added comfort and flex should you feel the urge to hit the dance floor. 

As for the rest, a rollneck sweater is never a bad idea. Unlike a regular work shirt, it suggests you’ve put some thought into how your outfit will play after hours. The same goes for shoes: instead of the usual Oxfords or brogues, why not swap them out for something a little unorthodox? A smart pair of sneakers or Chelsea boots by Hugo Boss are a tad more inspired.

The Winter Wedding

Black-tie dressing used to be just that: black, with a tie. Oh, how far we’ve come. Now, the colour of your jacket no longer needs to conform to such strict criteria, but we’ve bent the rules enough that we’ve done away with the tie requirement, too. In certain circumstances, that is. Unless you’re an up-and-coming bright young thing about to saunter up the red carpet at the Met Gala, you’ll probably still need to wear a dickie bow for the most formal occasions. But a winter wedding where you’ll be surrounded by friends? You can afford to colour outside the lines. 

Colour is the operative word here. Where fabric is concerned, it doesn’t get more festive than velvet. Especially when it’s in a rich shade of burgundy such as this handsome smoking-style Helward jacket (which, fortuitously, is also available in navy if you’d prefer something less exuberant). The accompanying trousers are a simpler affair, but no less elegant. Tailored from Super 120s virgin wool, they’re neatly tapered and trimmed with silk side stripes to match the jacket’s sharp peak lapels.

As winter weddings tend to get a little, well, wintery, you’ll find that rollneck will come in handy once again. Fellow guests will likely applaud your ingenuity when, if experience is anything to go by, you inevitably end up spending most of the evening in a draughty marquee. 

The Client Christmas Party

What was that we were saying about tuxedos traditionally being black? In fact, if sartorial lore is to be believed, the very first tuxedo was blue. “Celestial blue” to be precise – commissioned by the Prince of Wales (and future King Edward VII) in 1865, who tasked his Savile Row tailors with fashioning him a more comfortable evening jacket to wear to informal palace dinners. It took a further half a century or so before it was considered smart enough livery for the formal ones. 

Today, a tuxedo is a wardrobe stalwart representing the extraordinary things a tailor can do with a bit of cloth and several hundred well-placed stitches: the right one will help you stand taller, broaden your frame and streamline your profile. All of which is what makes a classic tuxedo the natural choice for a client party. Unlike when you’re on home turf, hobnobbing with the people who pay the bills is an occasion where it’s expected to err on the side of caution – and when it comes to style, that means keeping it traditional.

Observing the rules presents a singular dilemma, though: how to mark yourself out as a stylish individual, while remaining respectful to the dress code? A wise man would take a leaf out of the prince’s book, and opt for a midnight-blue tux, long touted by Hollywood’s seasoned stylists as more photogenic than black but still a relative rarity in the real world. This virgin wool two-piece from Hugo Boss, with its keen notch lapels (considered more forgiving than the shawl variety), satin trims and slim silhouette, will single you out for all the right reasons.

The New Year’s Eve Bash

Have we mentioned velvet already? There are manifold reasons why it crops up again and again in any festive style guide. For one, it’s warmer than most other fabrics, and therefore a smart choice for this time of year. But velvet also conveys an opulence that’s best appreciated in the twinkling lights of disco balls and fireworks, making it particularly well suited for New Year’s Eve. Yes, you may be heading back to the office bright and early on 2 January, but for one jubilant night you can live (and dress) like a king. 

Every man should arm himself with this attitude when the prospect of a NYE bash arises. To replicate the look above – which, as it happens, is precisely the sort of thing we imagine being worn by a particularly rakish attendee at Mr Truman Capote’s infamous black and white ball – equip yourself with Hugo Boss’ two-piece Henry tux in plush black velvet. To avoid hogging the limelight – there is, after all, only so many ways to respond to the inevitable barrage of compliments heading your way – keep everything else simple: add a pristine bow tie (to match that crisp white shirt), a gleaming pair of mother-of-pearl cufflinks and polished Derby shoes.

The Collection

  • Hugo Boss Navy Helward Slim-Fit Satin-Trimmed Cotton-Velvet Tuxedo Jacket

  • Hugo Boss Navy Helward Slim-Fit Satin-Trimmed Cotton-Velvet Tuxedo Jacket

  • Hugo Boss Navy Henry Slim-Fit Silk-Satin Trimmed Virgin Wool Tuxedo

  • Hugo Boss Grey Slim-Fit Puppytooth Virgin Wool Suit