Unless you count yourself among that rare group of responsible adults who complete their shopping before the first frost, you’re probably staring at a half-empty gift list with mounting unease. Holiday shopping, after all, breeds its own little ecosystem of anxiety – a blend of performative cheer, desire to get the perfect gift and the nagging suspicion that other people are better at this than you. We entertain a cinematic fantasy in which we wander serenely through festooned aisles, holiday music tinkling overhead, only to emerge triumphant when the recipient dissolves into grateful tears. The reality, as usual, declines to match the myth. December compresses time, crowds swell and we’re left holding our purchases like uncertain props. Consider, then, a few strategies that might make this annual ritual feel a bit less fraught.

Choosing a gift can feel unnecessarily stressful. We want to delight and surprise, of course, but we also fear getting it wrong and this stress is often directly proportional to how much we care about the person. This is one of those paradoxes of gifting: the more we care, the clumsier we feel. Still, the secret to finding a good gift is simpler than most people assume.

A good gift is about recognition. Inspiration doesn’t always come from store shelves or gift guides, but rather from how well you know the recipient. What do they mention liking? What small frustrations do they bring up? What type of hobbies or rituals shape their day? The best gifts start by collecting these little clues – the offhand comments, the preferences, the brands and sizes – and tucking them into your Notes app for the future.

Take the friend who seems to know everyone and is forever hosting. For them, a bit of fancy barware rarely goes amiss – a Ralph Lauren or Soho Home decanter, perhaps, or a set of crystal glasses, even one of those fancy ice buckets that adds a touch of ceremony. For the more retiring sort, the friend who would happily skip the party in favour of a quiet night at home, the register changes. Think pyjamas by Derek Rose, a Drake’s shawl-collar cardigan, or a throw from Johnstons of Elgin that give a reason for staying in.

Gift shopping is about letting your loved one know you’ve been paying attention to them and their inner life. Begin with who they are. Are they practical by nature or inclined toward sentiment? Do they thrive in company or cherish quiet time? Do they prize things or the memories attached to them? Even the humblest object – a scented candle, say – can take on unexpected weight if it recalls something shared. “This scent reminds me of our camping trip in July,” and it’s suddenly the right thing.

Clothing is its own minefield; it’s intimate in a way other gifts aren’t. And since clothes operate as a kind of social language, giving them can feel uncomfortably close to choosing someone else’s lines. Then there’s the matter of fit and size, which only heightens the sense that this can go sideways fast.

One way around the clothing dilemma is simply to go for an accessory. A leather work bag makes sense for the newly minted graduate who’s looking to hit the job market; a cashmere scarf is perfect for the friend who’s always cold. Spending a little more than your recipient would feel comfortable spending on themselves can also be a way to give the item a sense of occasion.

Alternatively, knitwear gives you a wider margin for error, as it’s far more forgiving than anything woven, which helps enormously when you’re guessing someone else’s size. If you’re intent on giving clothing, you could do worse than a sweater. For instance, a Shetland knit can add visual interest to an outfit, as it has a spongey texture you don’t get in the plain, smooth merino wool styles. In a versatile colour – navy, steel grey or chestnut brown – it can work with everything from a pair of classic flannel trousers and a waxed cotton jacket to more directional lines such as LEMAIRE or Dries Van Noten. Plus, since Shetland sweaters are both durable and easily mended, they offer the comforting promise of a garment that will be loved for many winters to come.

Shopping for colleagues is usually straightforward – those gifts tend to hover in the “butter-dish level” of things. But once the circle tightens to friends and family – the people whose preferences you really care about – there’s no harm in asking them what they want. In fact, the conversation can become its own small pleasure, a prelude to an outing or an experience you end up sharing.

Take the mechanical watch, that classic milestone gift. It can be a lovely gesture when someone’s just earnt a promotion or finally admitted they’ve fallen down the horological rabbit hole. But the category is a labyrinth, and the smallest things – how a case settles on the wrist, the faint tug of an automatic versus a manual wind movement – end up mattering far more than you’d think. Some men want the crisp elegance of a Cartier Tank. Others lean toward the clean lines of a NOMOS Glashütte. When it becomes a dilemma, the smartest gift is often the simplest: “Let’s go watch shopping together.”

Letting the recipient choose takes the sting out of an expensive gamble, and the process itself often becomes the part they remember. And really, you don’t have to land the bull’s-eye on your own every time. The whole exercise works best when the other person’s preferences sit at the centre of it. That’s the engine of good gift giving.