How to Navigate Gifting Season While Keeping Your Cool

Etiquette and shopping experts offer advice on some of the most common holiday issues, including wish list taboos, the politics of regifting and climate-conscious gift wrapping.

Credit...Giacomo Gambineri

Holiday gift-giving can be a daunting task no matter how long you’ve been at it. Luckily, help is here. We polled a number of gift and shopping gurus to tackle a host of frequently asked questions and to solve those gift-giving dilemmas.

Drawing up a wish list can benefit everyone involved: It relieves stress for the giver, it ensures you get something you really like and it makes sure no one’s time or money is wasted. Still, wish lists should be handled with care. Hanna Donnelly, a professional shopper and the owner of Hanna Lee Style, recommends that if you’re going to dole out a wish list, you should ask for one first. This will help the whole exchange feel less awkward.

It’s also useful to be a little vague. “I’d suggest not being too specific with your lists so as to maintain at least a bit of the surprise,” says Hugh Lagrotteria, a co-founder of the gift recommendation site Outdone. For example, you could put “cozy slippers” on your list but forgo providing a specific brand or URL.

“Children are so much happier than adults on their birthdays or on Christmas Day,” said Patrick Kucharson, who runs the newsletter Better Gift Coach. Why? Because children get gifts they like, since adults routinely ask them what they want instead of guessing. So don’t be shy about asking — though how you ask matters. “Phrase your question so it’s not about your need, but rather about showing interest in them,” says Laura Jennings, the founder of the gifting site Knack. “‘Is there anything you’re really loving right now?’ is going to generate better ideas than ‘What should I buy you?’”

It’s 2022: Let’s normalize regifting!

“Regifting with the intention of reducing waste and giving the gift to someone else who might appreciate it more than you do is, in fact, honorable,” says Jennifer O’Hare, the chief executive of the artisan gifting site Belle Box.

But a wise regifter should put a healthy amount of space between the person who originally gave the gift and the person who receives it. Make sure those two people aren’t in the same social circle to avoid any hurt feelings.

“I know most people in my life would prefer this to the alternative of the gift sitting in the closet collecting dust,” Mr. Lagrotteria says, “especially as people become more conscious of overconsumption.”

You should feel especially empowered if the giver included a gift receipt. That’s what it’s there for! And if you are a serial exchanger, practice what you preach by tucking gift receipts into your presents whenever possible.

Gratitude is obligatory, but panic shopping out of guilt is not. Sabira Bandali, the founder of the online magazine Haul of Fame, suggests that if you’re caught empty-handed, just express your sincere thanks either in person or in a note, and then surprise the giver with a gift at the next occasion that warrants one.

Gifting up, or buying for your managers, should not be an expectation. You give the gift of time and energy to them on many other days of the year. However, the holidays are an excellent time for bosses to show their appreciation for their team members with a thoughtful holiday gift. And what if a co-worker unexpectedly hands you a wrapped box? See the previous answer.

The consensus is clear: Cash is king when it comes to thanking the people who make our lives easier all year long. The gesture is stronger, though, if you include a handwritten note and give it to them directly.

In terms of numbers, a good rule of thumb when gifting cash to someone you regularly pay, such as a housekeeper, is to give them whatever their usual fee is again as a holiday bonus. If you’re gifting money to someone you don’t typically pay, such as a building superintendent or a security guard, simply give as much as you reasonably can. What’s generous for you may be more or less than what’s generous for your neighbor, but the important thing is you’re being just that: generous. And if you’re on a tighter budget, that handwritten note or some homemade baked goods can help to show your appreciation.

(A note about postal workers: They are not supposed to accept cash or even gift cards, but they can accept a gift worth $20 or less, so something like artisanal coffee or candy would be a suitable choice.)

D.I.Y. is the way to go, says Mr. Kucharson. If you’re smart, one project can go the distance by making a single gift cover multiple people. For example, you could digitize old family photos or videos and share them with every member of the family. Other no-budget ideas include babysitting, planning a hike or a beach day, compiling a digital recipe book or creating a personalized playlist.

“A lot of etiquette involves us, as a society, all agreeing on certain fictions,” says Nick Leighton, the co-host and producer of the etiquette podcast “Were You Raised by Wolves?” “For gift cards, the fiction is, ‘This is not cash.’”

But gift cards can also do something money cannot: show the recipient that you thought about what they like and where they shop, and that you want them to treat themselves. It discourages saving and encourages living a little — and that’s a real gift.

Any donation is an act of kindness, but what makes one a good gift is whether it goes to an organization your loved one is especially passionate about. Picking a cause close to their heart shows you care enough to pay attention, which is what makes any gift great.

Every expert we spoke to agreed on one thing: No one can agree on this. Every family is going to approach this differently, which means communication is key, especially if you have a large contingent of relatives. But in any family children should be the ones raking it in. Showering the little ones and slowly phasing out each generation as they age is the typical move. That may mean you receive fewer gifts, but it also means you don’t have to buy as many for your peers. And if you’re someone with kids, it means there are more people to help you tick off the items on their lists. Win-win-win.

Start them young, Mr. Kucharson suggests. “One of the greatest feelings in the world is being excited to give someone a good gift,” he says. “We make a point to include our 3-year-old in the selecting, wrapping and presentation of gifts to his cousins and friends.”

Anyone who has a birthday in December is going to say no, and that’s who we should listen to on this. That said, if there’s a more extravagant gift you know this person would love, its value adds up to what you would otherwise spend on multiple gifts and you really, really feel like it should cover everything, try this: Give that gift for the more personal occasion and pick out a small, inexpensive but thoughtful gift for the holiday. That way the recipient gets each of their moments acknowledged, and you don’t go broke.

Eco-friendly gifting has been trending for years, so we’re all familiar with the typical stuff: using newspaper and other recyclable materials for wrapping, reusing gift bags and upcycling or thrifting gifts. Mr. Leighton has an additional suggestion: furoshiki. These traditional Japanese fabric wrappers can be used over and over, making disposable options obsolete.

“Besides looking incredibly chic,” he explains, “it’s also way more environmentally friendly than wrapping paper.”

Getting something you need is always going to be appreciated, but does that truly make for the best gift? Your gut is probably saying no. “People will naturally buy themselves what they need, but they’re hesitant to make those big splurges,” says Ms. Bandali. “That’s where you come in.”

Ms. O’Hare agrees: “An unexpected gift over a useful gift wins every time.”