Avoid brown in town. Or after 6.00pm. And never do business with a man in loafers. These are some of the shoddy truisms our grandfathers taught us as callow lads. We also remember the intoxicating confusion of entering a proper bootmaker’s for the first time. The experience was not that different to being hungry and in need of a stiff drink in a foreign land. Staring at the array of bench-made shoes as a well-meaning salesman prattled on was as disconcerting as that Scandinavian misadventure when we thought we ordered a steak and received cold mackerel.

“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.

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.

James Dean in the 1950s. Robert Redford in the 1970s. Michael B Jordan last year. The shearling jacket is outerwear for those who like their cool factor with a side of sophistication. This is baked into the design. Whether it’s the aviator and bomber styles of Loro Piana and CELINE or the longer coats of BODE and Brunello Cucinelli, it has the kind of blue-chip pedigree that other outerwear can only envy.

Avoid brown in town. Or after 6.00pm. And never do business with a man in loafers. These are some of the shoddy truisms our grandfathers taught us as callow lads. We also remember the intoxicating confusion of entering a proper bootmaker’s for the first time. The experience was not that different to being hungry and in need of a stiff drink in a foreign land. Staring at the array of bench-made shoes as a well-meaning salesman prattled on was as disconcerting as that Scandinavian misadventure when we thought we ordered a steak and received cold mackerel.

“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.