We may be in the final throes of 2016, but the year that brought the menswear world bomber jackets, relaxed tailoring and more trainers than a Supreme store on drop day is still far from over as far as your wardrobe is concerned.

The onset of the Christmas season brings with it weekends spent in shops, evenings spent at bars and the occasional day spent, however reluctantly, dressed in a novelty jumper.

Each of these yearly rituals is as unavoidable as the next, so you might as well look on-point while taking part. Here, then, is a seven key date guide covering every event from now until 2017.

Christmas Jumper Day

The only person worse than the rabid colleague forcing everyone to wear a wacky Christmas jumper is the miserable git who refuses. Don’t be that guy. If you can’t get on board with a festive knit once a year, don’t be surprised if you’re visited in the night by three ghosts.

If you’d prefer a good night’s sleep, scout out a jumper made from 100 per cent wool. Cheaper examples tend to be made from polyester, which puts the ‘sweat’ into sweater. Opt for a design that is only subtly festive, like this snowflake design from Tokyo-based label Beams Plus, so you can enjoy its warming properties well into the New Year.

(Related: The 6 knits you should own this season)

Styling Suggestion

Men's Festive/Christmas Jumper Outfit InspirationNext

Key Pieces

Men's Festive Jumpers

Next Grey Snowflake Christmas Jumper - Click to buyBEAMS PLUS Intarsia Wool Sweater - Click to buyJ.CREW Fair Isle Wool Sweater - Click to buyAMI FAIR ISLE CREW KNIT Grey & Black - Click to buy

Christmas Shopping

If you plan on doing your Christmas shopping in your pants (online that is), congratulations, you can skip this section. If not, chances are you’ll need something smart, comfortable, warm and breathable to survive the high street.

If that all sounds like a contradiction in terms, take a leaf out of the athleisure playbook and team joggers with a well-cut overcoat for the wise man’s way to look presentable and feel snug.

A pair of running trainers with a cushioned sole will also keep you ‘Walking in The Air’ even when you’re weighed down by bags.

Styling Suggestion

Men's Christmas Shopping Outfit InspirationRiver Island

Key Pieces

Men's Christmas Shopping Outfit

Reiss MAPEL DOUBLE-BREASTED COAT - Click to buyZara OVERSIZED COAT - Click to buyH&M Marled sweatpants - Click to buyNIKE AIR PRESTO - Click to buy


An office Christmas party is only a cause for concern if you fail to read between the lines and end up judging the dress code incorrectly.

Is the word ‘ball’ on the invite? Are you going to an expensive-looking hotel? You’ll need a tuxedo. Shawl collars (a rounded piece of satin that extends down the front of the jacket) are flattering for all body shapes, with traditional English tailors such as Hackett and Gieves and Hawkes offering some of the best examples.

If your budget doesn’t stretch, more affordable versions can be found on the high street. Just remember that fit is key and no matter the cost of the jacket, a little tailoring always goes a long way.

(Related: The complete guide to modern dress codes)

If the dress code isn’t black tie, revert to a blazer (try a velvet or double-breasted option) with dark trousers and smart shoes. This look can be dressed up with a shirt and tie or roll neck, if the party’s a cracker, or down with a T-shirt if it’s a turkey.

Styling Suggestion

Men's Christmas Party Wear Outfit InspirationHugo Boss | Mango Man

Key Pieces

Men's Partywear Blazers and Trousers

Charles Tyrwhitt Black slim fit shawl collar tuxedo jacket - Click to buyReiss ISLAND DOUBLE-BREASTED WOOL BLAZER BURGUNDY - Click to buyMango Man Velvet Shawl Blazer - Click to buySELECTED HOMME Black Smart Trousers - Click to buy

Christmas Eve

Call us conservative but the night before Christmas is not the time to trial a new, Vetements-inspired, elongated, post-sportswear silhouette; especially if you’re attending Midnight Mass.

If headed to the pub, go for what you’d usually wear – i.e something you feel comfortable and stylish in. A shirt over a T-shirt is a good place to start. Abercrombie & Fitch, a name not often mentioned for its restrained interpretation of classic workwear, makes an excellent overshirt that feels relaxed but not scruffy when flanked by a white tee. Even better, it’ll add an extra layer of ballast under your coat when queuing for a Christmas eve taxi home, too.

(Related: Why you should own an overshirt)

Styling Suggestion

Men's Christmas Eve Outfit InspirationMango Man

Key Pieces

Men's Christmas Eve Outfit

ACNE STUDIOS SONTAG TWILL OVERSHIRT - Click to buyAbercrombie Stretch Garment Dye Shirt Jacket - Click to buyJaeger Organic Cotton T-Shirt - Click to buyUniqlo Stretch Selvedge Slim Fit Jeans - Click to buy

Christmas Morning

There are plenty of mornings in the year when it’s acceptable to wear pyjamas. But this is Christmas morning. Your family have made an effort, bought you presents, filled a stocking. The least you could do is treat them to a master class in loungewear.

Knitted trousers will look presentable but still feel like you’re between the sheets. Then, cheat on the top half using a granddad collar top – David Gandy’s expert range for Autograph at M&S includes an excellent example – and Santa’s your uncle, you’re dressed without getting dressed. Pass the bucks fizz.

(Related: How to look like David Gandy between the sheets)

Styling Suggestion

Men's Christmas Morning LoungewearH&M

Key Pieces

Men's Christmas Morning Loungewear

M&S Supima Long Sleeve Pyjama Top- Click to buyUniqlo Waffle Henley Neck T-Shirt - Click to buyJoseph Loop Back Knit Trackpant - Click to buyCOS KNITTED CASHMERE TROUSERS - Click to buy

Christmas Day

Happy fancy shirt day! Now that you’re out of your loungewear, it’s time to make even more of an effort, or at least, make it seem that way. In 2016, people cottoned on to the fact that a statement shirt was a very simple way to dress up. During the summer that meant Hawaiian prints. In the winter it’s as simple as a panel of contrasting colour, as seen on this shirt from chic French brand Ami.

Button the collar all the way to the top pre-lunch before relaxing to give your gullet some room if necessary. Jeans with this will do, but a pair of black, tailored trousers signals real yuletide dedication.

Styling Suggestion

Men's Christmas Day Outfit InspirationReiss

Key Pieces

Men's Christmas Day Shirts and Trousers

Reiss OCELLA EMBROIDERED SHIRT NAVY - Click to buyAmi Shirt - Sky Blue - Click to buyRiver Island Navy textured trousers - Click to buyACNE STUDIOS Max Slim-Fit Overdyed Denim Jeans- Click to buy

Boxing Day

You might have spent the last 36 hours sat inside next to a fire, slowly poaching in wine and insulating yourself with turkey, but a Boxing Day walk is not the time to rock a flimsy jacket from the back of the wardrobe.

It’s cold out there. Shrug on a down-filled parka and take the warmth with you. Canada Goose is the gold standard in high-quality, good-looking protection from the elements, but its outerwear doesn’t come cheap.

(Related: How to wear the puffer jacket)

Luckily there are plenty of brands that also make great, warm coats. Vans, for instance, has recently launched its all-weather MTE collection, which includes insulated Old Skools and water-repellent quilted bombers.

Styling Suggestion

Men's Boxing Day Walk Outfit InspirationSimons

Key Pieces

Men's Outdoors Jackets and Shoes/Boots

Canada Goose Citadel Parka Coat - Click to buyUniqlo Down Hooded Jacket - Click to buyDIEMME ROCCIA VET BOOT Mogano Original Leather - Click to buyVans SK8-HI MTE - Click to buy