A fine balance of the intangible element of surprise, the cold, hard numbers of sizing and your powers of telepathy – buying gifts for folk can be a tinsel-strewn, pine-dotted minefield. With that in mind, when drawing up your list, it is always wise to mark out the particularly tricky customers you intend to impress. In bold, capital letters: fathers and brothers.

After all, we tend to know these people inside out. We are expected to understand their likes, dislikes and whims. And, generally, they have no fear in telling us exactly what they think. So, the pressure is on to get things right. Worried? See if what we’re gifting, below, inspires you this holiday season.

My youngest brother is something of a high roller. He’s got the fat job in New York, the house in the Hamptons and the beach on his doorstep. When he’s next paying for an artisanal coffee and a pastry in Sagtown Coffee in Sag Harbor, I’m hoping that pulling out this gorgeous burnished-leather billfold wallet by Brunello Cucinelli will remind him of his big bro, of all the things I have done for him for over the years, and of why he really needs to buy me a present that’s just as classy.

Call it lack of imagination (or a long-standing tradition), but every year for as long as I can remember, we have got my grandad a shaving set for Christmas. He doesn’t have a Santa Claus-like beard to attend to, but, at 82 years old, he is of the generation that thinks a bit of stubble is “rather scruffy”. This year, this rather festive Floris London shaving set will be sitting under the tree for him – because if it’s good enough for shaving the kings and princes of England, then it’s good enough for my grandad.

When I was a kid, I bought my dad a brand new LL Bean briefcase (embroidered with his initials, natch) for him to bring to his job at the United flippin’ Nations. I was very proud of the gift, and he seemed genuinely chuffed. In retrospect, it was a ridiculous bag for a man going to work at a massive international governing body. Today, I would probably choose something like this Bennett Winch, which is a sleek upgrade to the navy canvas, baggy-cargo pocket bag of yesteryear, but is still low-key enough that it doesn’t scream “I’m the fanciest man on the Subway”. This is also a good starter bag for a brother who’s just gotten a new job, or who has been carrying his stuff to work in a free tote. Briefcases are not for nerds – prove it to them with a gift like this one.

I am from The North (the bit on the map of England that isn’t London). We cannot be trusted and we do not contribute much. We are an uncouth, unsophisticated breed and we are incapable of laughing or gesticulating in a restrained manner. So, it is quite right that we are not allowed to drink beer with a portion of chips, or see our loved ones at the moment. With limited ways to give gifts to my brother or father this year in person, I am free to buy whatever I please, to push their limits of taste, safe in the knowledge that the only person they can express any potential disappointment to is the postman. Merry Christmas, Father.

My dad – as is right and proper – likes to get good wear out of things. He’s also a man who values practicality in his clothing. Nothing wrong with that. And he spends a good deal of time outside for work (he advises on the preservation of historic buildings). But things have come to a head: a certain “construction-site chic” (read: yellow and silver hi-vis) has crept in, and not in a good way. He needs a coat upgrade and this Moncler fits the bill – warm, dignified, but not dull, and blessed with ample pockets.