“He who is not courageous enough to take risks will accomplish nothing in life,” as Muhammad Ali once put it. But can that theory be applied to buying gifts? You don’t want to be the guy who gives everyone the same thing every year. But we’ve also all at one time or another given or received a gift that didn’t fit or wasn’t quite right or was taken as a personal slight and had you ejected from the building post-haste (just us?), so you’ve got to ask yourself if it’s worth the punt.

This year, you could play it safe. Get something classic, a piece that everyone has a need for and that won’t require a receipt. Or you could roll the dice and put your faith in the one grand gesture that could win (or lose) the whole holiday season. Either a timeless investment piece that may seem uninspired, but they’ll make use of forever. Or immortality with the present they’ll never forget, hopefully for the right reasons.

Which is the right route to take? Only you can answer that. However, two of the MR PORTER Team have their own thoughts.

By Emma Pradella, Brand Partnerships & Marketing Editor

You’ve already received your fair share of Wish Lists – or unsolicited gift requests, if you will – survived the multitude of parties and sheer breadth of office functions; you will have likely discussed the menu, the guest list and seating plan of your own family’s Christmas dinner in depth… And if that wasn’t enough, you’ve still got to get the gifts (and wrap them).

It’s very Grinch of me, but for the sake of maintaining your sanity over the festive period, may I introduce you to the real unsung heroes of the holidays – classic, dependable gifts that won’t disappoint anyone. Not only do they preserve reputations, ensuring you still pass as the thoughtful gift giver you claim to be, but they also prevent any regifting scenario – or your recipients having to awkwardly ask you for a gift receipt, at least.

But forget the hassle of gift giving for a second – say you actually enjoy the process. The plus of playing it safe is that whatever you get them has the potential to become one of their most loyal life companions. Think of a reliable navy sweater made by some of the best in the business; a pebble-leather cardholder; a pair of special socks they may not buy for themselves on the regular; a warm scarf or uber-soft beanie they can wear with anything. Who doesn’t need these things? Exactly.

By Jim Merrett, Commissioning Editor

The Art Of War by Sun Tzu clearly isn’t a treatise about buying your loved ones the best gifts. It predates Christmas itself by at least 400 years, for one. However, its framework can be – and has been – applied to most competitive endeavours. And you better believe buying presents for others counts as such.

Much of what the great Chinese military strategist had to say considers the best use of resources, which is certainly relevant in this case. But more than anything, his tactics touch on human psychology and the perception of the best use of resources. Know your enemy (read: gift recipient) as you know yourself – or at least better than they know themselves – and buy a gift accordingly. Also, while invincibility lies in defence, the possibility of victory is in the attack. And what is a big-impact gift if not a statement of intent?

All of which is to say that a risk isn’t a risk when you’ve done the groundwork. And a navy sweater, like last year, might be all they’re expecting. However, after the event, a jazzy cardigan will be the piece they remember.

In part, you’ll need to observe. Not just what they think they need, but what are they missing? What’s their style, but also what could be their style? Then, sow the seeds. Set them up for disappointment, only to wow them with something unexpected. Or convince them that whatever you’ve gifted them isn’t just a nice thing to have, it’s the key to unlock their potential. A new life starts here. And the catalyst for that isn’t slippers, a wallet or a pair of socks. (OK, maybe a particularly characterful pair of socks.)

Win the psychological war and you win the war itself. Failing that, everyone could do with a good book. (Have they read The Art Of War by Sun Tzu?)