Remember when we used to talk about Christmas “getting earlier every year”? The good old days when the festive season would creep up on us insidiously rather than dumping itself, like a truckload of glitter, all over our towns and villages at midnight on the first of November? Hearing the familiar strains of “Do They Know It’s Christmas?” while standing in line for a coffee in early November, it’s not anger or disappointment that washes over us now but ennui: a sense of grim resignation at the inevitability of it all.

It’s in that spirit that we present you with our very own holiday gift guide. Is it early? Yes. But we’re also fully aware that many of you do like to get ahead of the game. It’s a smart move, too. You want to give yourself as much time as possible because gift-giving is a high-stakes game. Get it right and there’s a lot to gain. Get it wrong and at best you’ll betray a lack of thought, at worst a fundamental misunderstanding of your intended’s personal taste. It’s only natural, then, that you might enter into the process with a degree of trepidation. To assuage your fears, we’ve asked a series of experts in the field of nice things – from menswear and womenswear to watches, homeware and grooming – for their advice on how to pick the perfect present.

Mr Alan Bedwell is the owner of Foundwell, a purveyor of fine watches and jewellery. Also a passionate collector, he lists vintage TAG Heuer timepieces of the late 1960s and 1970s as among his all-time favourites. Read on for his tips on how to choose a watch that he’ll cherish for ever.

“Try to choose a watch that’s likely to fit. This goes especially for smaller, slimmer men, who simply won’t look right with a 44mm watch on their wrist. Consider what he wears, too. If he prefers cuffed shirts, a slim dress watch is your best choice.”

“Buying him his first proper watch? Your best bet is to play it safe and choose something versatile that he can dress up and down. Don’t buy him a big sports watch. If he already owns five or 10 watches, that’s a different story – you can be a bit more adventurous.”

“Choosing the perfect watch should be like playing a game of Guess Who? Ask yourself a series of questions: do they want a dark dial or a light dial? A bracelet or leather strap? A military watch or a dress watch? How much are you willing to spend? Narrow down the selection until you’ve found what you want.”

Choosing a gift for the woman in your life is not only the trickiest decision you’ll make all festive season – it’s also the most fraught with peril. This is one you really don’t want to get wrong, which is why we suggest putting your faith in the advice of Ms Kay Barron, Fashion Director of NET‑A‑PORTER and a woman with a lifetime’s worth of experience of receiving gifts from men – some good, some not so good. (The gifts, not the men.)

“The first thing to remember when buying for a woman? Don’t buy her something she’d buy for herself. It doesn’t matter how expensive it is, or how lovely the cashmere – women don’t want to unwrap another sweater on Christmas morning. This isn’t the time for stocking up on basics. Don’t be sensible. Be decadent.”

“If you’re thinking of buying her jewellery – and you should be – keep it classic and take your cues from what she’s already wearing. If she wears mostly gold, don’t buy her something made from platinum. If she prefers minimal jewellery, don’t buy her something ornate.”

Whatever you do, don’t leave it until the last minute. Not only will you find yourself throwing money at something horrid and overpriced out of sheer desperation, you’ll have missed out on the signals, too. If she has a particular gift in mind, she will have been subtly telegraphing her desires for weeks, if not months, in advance.”

Mr Mubushar “Mubi” Ali caught the sneakerhead bug while he was still in his teens. Now 38, he has amassed a collection of roughly 4,500 pairs and has worked as a sneaker consultant and designer for brands including Nike. So, what’s the appeal of sneakers? He puts it down to a combination of nostalgia, street cred and, of course, exclusivity. “It’s about looking different,” he says. “Standing out from the usual.” Here, he shares his expert tips for this coming holiday season.

“This winter, it’s all about the outdoor trend. It’s a hot topic for a lot of the big sneaker brands, so expect to see them reintroducing older models that were popular back in the day. Nike is bringing back ACG, its “All Conditions Gear” line; adidas is bringing back Terrex; Salomon is doing a lot of great heritage stuff as well. Don’t forget: winter’s a time when you can expect a lot of bad weather, so these are a practical choice, too.”

“Retro running dominated 2019. Nike reintroduced two of its earliest running shoes, the Tailwind and the Daybreak; adidas revived its own heritage models; and at the upper end of the market we had Fear of God’s Jerry Lorenzo debuting a retro running shoe, too. Expect this to continue into the new year with fresh collaborations from Sacai and Nike, and much more. This is one trend that’s going to run and run.”

“If you’re not sure what to buy someone and you’re looking for a safe bet, go with something classic. New Balance makes some of the best, most comfortable sneakers out there. They’re timeless, low-key and look good on anyone. And, if you want something a bit bolder, the brand has done some great collaborative work with brands such as Pop Trading Company, Comme des Garçons and Engineered Garments.”

A grooming journalist who landed his first job in the industry in the mid-2000s, Mr Ahmed Zambarakji has watched as moisturiser for men has gone mainstream. Fragrance, skincare and haircare products are now some of the most popular gifts during the holiday season. Here, he offers his tips for how to choose something that’s not only tasteful, but personal.

“Steer clear of anything that might be deemed corrective. This includes thickening shampoo and anti-ageing cream. Much as I approve of the ‘Doctor’ brands, their approach to skincare is very much about finding a solution to a problem. That might be taken as an insult.”

“Men are creatures of habit. If you try to add an entirely new element to their grooming regimen, it’s likely to end up gathering dust. Instead, look at what they’re doing already and find a way to upgrade it. If they shave every day, why not give them a better razor or a post-shave serum?”

“Fragrance is an extension of a man’s personality. If he sees himself as dark and brooding, he might not appreciate a zesty, floral eau de toilette. Look for clues in his life that might offer some guidance. What’s his favourite season? What kind of food and wine does he like? His wardrobe might tell you something, too.”

Mr Charlie Teasdale is the style director of British Esquire and one of the most respected names in the men’s fashion industry. “Clothes are a tricky thing to buy for someone,” he says, “because style is ultimately a personal choice. If you don’t get it right, he simply won’t wear it.”

“Don’t be afraid to choose something understated, especially with people you don’t know that well. As long as it’s of a superior quality, he’ll appreciate it. Think of a tie from Charvet or Drake’s, a T-shirt from Sunspel or a sweater from Brunello Cucinelli or The Row. They may be simple things, but they’re the best you can buy.”

“Not sure which size to buy? Go a size up. It’s much simpler to tailor larger clothes to fit. You can take fabric away, but you can’t put it back in. Plus, it’s much less offensive to buy something that’s too big than too small.”

“If you’re buying for someone younger, such as a son or a nephew, do everything you can to get inside his head. Don’t be afraid to ask advice from his friends or his partner and check his social media to find out if there are any brands he likes.”

A cultural historian and lecturer in contextual studies, Dr Benjamin Wild specialises in the history of fashion and the decorative arts. The trick to buying a gift, he says, is to consider not just what it is, but what it might become. “Inanimate objects – a pen, a brooch – can become so imbued with meaning,” he says.

“When choosing a gift, try to look beyond the initial moment of giving and consider the ongoing experience that that gift will provide. Think of a candle, which is a joyous thing to unbox, but also gives your recipient hours and hours of pleasure. Choose gifts with longevity.”

“Gifts that relate to some shared experience will hold a deeper resonance than something that is merely beautiful. Did you go on holiday or visit a gallery together? Something that sparks that shared memory will always be cherished, and will always remind them of you.”

“If you’re buying a gift for a new partner or a work colleague, you may not have been to their home and had a chance to assess their taste. Try to understand the connection between what a person might put in their house and the way they represent themselves in other ways, such as how they dress.”