How to Regift and Get Away with It

A guide to the perks and pitfalls of giving used gear for the holidays. By Christy Harrison

Often the most treasured gifts—family heirlooms, old books, paintings, vintage clothing, jewelry—have had past lives. And whether you choose antique, vintage, or just, ahem, “previously loved” items, giving used gifts can be a great way to help out the environment (not to mention your bank account). Old stuff doesn’t come wrapped in layers of manufacturers’ packaging, so buying used means you’re helping to minimize holiday waste; and, of course, you’re rescuing someone else’s castoffs from the dump. Best of all for the buyer, picking out gifts in thrift stores or online reduces the trapped-in-the-mall anxiety that the holidays can provoke. But Aunt Doreen probably wouldn’t appreciate that 1980s Teenage Mutant Ninja Turtles T-shirt the way your twenty-something friend would. And giving used stuff can be misconstrued as “re-gifting”, the quintessential holiday faux-pas. So when is it appropriate to give retreads, and who should get what?

Above all, experts say, make sure you’re familiar with your recipient’s tastes. “You have to know a person pretty well if you’re going to give vintage,” cautions manners maven Lesley Carlin McElhattan, co-host of the Web site After all, traditional low-intimacy presents, like fruit baskets or gift certificates, aren’t sold in thrift stores. Giving a vintage gift is a step into more personal territory with your recipient, a leap of faith—so be sure you’re ready. A good rule of thumb: don’t give your boss a set of 1950s highball glasses unless you’re willing to down a couple of White Russians with him after work.

Buying used also means that, in general, the person can’t return or exchange the gift, and that’s a big risk. Sadie, a book editor in New York City, says the worst gift she ever received was “an empty metal olive oil canister in the shape of a watering can—I didn't even have a plant.” At least unwanted gifts that are new can usually be redeemed for store credit.

Jake, a teacher in New York City, also knows the horror of the gift-wrapped hand-me-down. “Growing up, a family member gave me used gifts. They were things that didn't even match my taste, so the fact that they were used made them seem even worse. It came off as really random.” Givers of pre-owned gifts can seem even more out-of-touch than the average distant relative, so the perils (as well as the potential rewards) are greater.

Then again, some objects lend themselves better to vintage gift-giving than others. Clothing items and accessories are often risky, not only because they might not fit. “My boyfriend gave me a vintage pony-skin purse last Christmas,” says Emily, an actress in Berkeley, California. “He thought it was really cool because they don’t make them any more and it came from Mexico. I thought, ‘I am holding a dead horse. I am putting my keys into a little dead horse.’ Not the most romantic thing.” Perhaps another rule of thumb, then, should be: don’t give objects made from nontraditional animal pelts unless your recipient is into hunting. “I've only had success with used books, usually poetry, often out of print,” offers Elizabeth, a writer in New York City. The rarity of such literary presents can make them more appealing than brand-new titles. “I generally prefer to give people used books—they're more precious that way,” says Kamon, a lawyer in San Francisco.

Whatever object you choose, make sure it’s not too rough around the edges. “Generally, you don’t want to give something that looks like it’s been used a little too much,” says McElhattan. “Giving a first-edition antique book is okay, but giving the dog-eared paperback you took to the beach is not.” While this distinction may seem obvious, judgment can go out the window during the holidays under the stress of last-minute shopping.

Even with used gifts in excellent condition, givers may worry that they will be viewed as cheap; some people say they feel compelled to alert their recipient that their present has a past. But the jury is split on whether it’s absolutely necessary to confess. “You can include an explanation with the gift, but in most cases you’ll look really thoughtful for having gone onto eBay and getting the thing that [the person] had mentioned two months ago,” says McElhattan. But Lash Fary, author of Fabulous Gifts: Hollywood’s Gift Guru Reveals the Secret to Giving the Perfect Present (New American Library, 2005), is a big proponent of explanations. “Always come clean,” he says. “That way, you rob people of the power of finding out that your gift is used.” Of course, you don’t have to wax philosophical about why you buy used gifts—explaining a pre-owned present can be as simple as telling a funny story about it. “In your card, you can say something like, ‘Dad, you’ve always reminded me of Cary Grant, so I thought you should have something from the same era,’” says Fary.

What if you want to give something used that’s not from another time—that is, the notorious re-gift? If you’re short on cash for the holidays but have some really cool little thing lying around that someone gave you and you’ve barely even used, is it okay to give it to someone else, just this once? The only other option is throwing it away, right? Controversial questions, all. “Re-gifting is just fraught with peril,” says McElhattan. “It’s so hard to do it and get away with it; for me it’s not worth the anxiety. I’ve heard horror stories of people getting a gift and having another person’s card tucked inside the box.” Yikes. Fary has a solution, though: just re-pack and rewrap the gift, making sure there are no personal notes slid in between the cracks. And of course, he adds, always re-gift outside your close circle of friends. But with these caveats in mind, you can make a re-gift “something that really reminds you of the recipient—something you’re sure they’d love,” he says. “I’m a huge fan of re-gifting; the faux-pas only happen when people aren’t thoughtful about it.” When you re-gift, though, you’d often do better not to explain the present’s origins. “If a re-gift looks vintage or used you should acknowledge it; otherwise, a gift is a gift,” says Fary.

Even this rule has an exception, though: call it the re-gifting prank party. “One time, years ago, some friends and I got into another friend’s apartment and stole back all the stuff we’d ever given her, wrapped it up, and gave it to her again,” says Katie, a graphic designer in New York City. “It was the most fun birthday party ever—and the best part was that she didn’t even remember that she had some of the gifts in the first place.” With some creativity and thought, even the most obviously recycled presents can become a totally new source of joy