The party season poses some quandaries. The escalating demands on your diary require you to regularly swap office chair for bar stool, but rarely with the liberty of a trip home between. So what you wear needs to work twice as hard – and be twice as versatile – to take you straight from work to play.

The key is simple pieces that can be styled both ways. Enter the folks at menswear e-tailer Combatant Gentlemen, whose affordable collections are slick enough to carry you from quarterly reports, to your first Negroni, with a handful of subtle tweaks. It’s time to stop being a dull boy, Jack, and learn how to #HolidaySmarter.

Dress To Impress: From Day To Night

Combatant Gentlemen - Day To Night Pieces 2015

Combatant Gentlemen - Day To Night Pieces 2015

The Camel Coat

Outerwear is the key to your transition from office to out. But in your choice of coat lurks a series of pitfalls, ready to trap the unwary man. Steer too formal and you’ll be swerved all night, as people worry that you’ll find a way to steer every conversation back to year-end projections. But head too far towards casual styles and your colleagues will confuse you with the intern.

In the sweet spot sits the camel coat. Like its namesake, it’s a coat designed to weather every environment: the neutral tone is less stuffy than black or navy, but still sits pretty over any other shade; the mid-thigh cut is more modern and easier to move in than a knee-brushing overcoat; and because it’s single-breasted, you can wear it open to reveal the dressed-up-or-down outfit underneath.

To maximise versatility you want to take a cue from your tailoring and steer slim. Skinny fits are fine for the office, but are too formal for off-duty. And you’re best off leaving that oversized thing to Kanye, unless your CV is similarly avant-garde.

Combatant Gentlemen’s take keeps things classic with a soft shoulder and nipped in silhouette that pairs as happily with tailoring as jeans. So neither your boss, nor your date, will be left with the hump.

Priced $120

Combatant Gentlemen Camel Wool Overcoat

The Suit

For tailoring that goes both ways, you want to steer down the centre. Not season one of Mad Men, with a figure-hugging fit in shades as sober as Don Draper before 10am. Yet shy of Mad Men season seven, with billowing fabrics awash in acid-tinged patterns, which make you feel as tipsy as Don Draper after 10am.

Instead, look to Combatant Gentlemen’s guncheck, which switches boss-friendly navy into something more eye-catching. The construction relaxes things further, jettisoning padding for a soft shoulder – there’s that Italianate sprezzatura – and a half-canvassed structure that drapes, rather than constricts. And because the jacket’s cut slightly short, you can deploy it solo, with denim or chinos, for that European split-suit aesthetic.

Perfect for changing tone when you shutter those spreadsheets.

Priced $220

Combatant Gentlemen NAVY GUNCHECK SLIM FIT SUIT

The Work Shirt

As with your tailoring, block colours belong firmly in the boardroom. Some subtle texture adds visual interest and implies that you’ve got a life away from the office.

This shirt’s herringbone weave contrasts with the suit, especially if you finish the look with a knitted tie – in winter, variety in your fabrics beats eye-popping shades.

It helps that the Italian cotton is wrinkle-resistant, so that after a day spent bouncing between meetings, you can head straight out and still look freshly pressed.

Priced $35

Combatant Gentlemen BLUE MINI HERRINGBONE SLIM FIT SEMI SPREAD COLLAR SHIRT

The Out Shirt

Even better, of course, is to have a spare shirt stowed in your desk drawer (also wrinkle-free, naturally).

To look like you’ve not just stopped in for a quick one on your way home, you’ll want to embrace pattern. But be subtle. Combatant Gentlemen’s polka dot design nods to your new, boozier locale, without looking like you’re going to be the last guy to leave at the end of the night.

Priced $35

Combatant Gentlemen NAVY DOTTED SLIM FIT BUTTON-DOWN SHIRT

The Jeans

Remember what we said about that split-suit thing? Dark denim is your wingman here. And the inkier you steer, the better.

Simplicity pays dividends in design, too. Skinny jeans may be dead, but this is no time to dive into the wide legs that have started popping up on runways; a slim, straight-leg fit echoes your suit pants, ensuring your denim sits well beneath the jacket.

Let the hem length be a hat tip to where you’re heading. For post-work drinks, a quick turn-up to flash some ankle pulls your look firmly away from the office. If the boss is joining you, let them break on your shoes to reassure him that you won’t be coming in fuzzy-headed tomorrow.

Priced $45

Combatant Gentlemen NAVY BLUE SLIM STRAIGHT ENDURANCE DENIM JEANS

FashionBeans Exclusive Offer

For 15% off the Combatant Gentlemen range, use the exclusive code FBHOLIDAY at combatgent.com until 2 January 2016.

Check out the hashtag #HolidaySmarter for more seasonal, sartorial inspiration.