How to Win at Giving Presents

Technically, gift giving isn’t a competitive sport, but it never hurts to have a winning strategy. Plus 22 ideas for excellent presents!

Welcome to Hi Everyone. I’m so glad you’re here! If you’re reading this and haven’t subscribed, please consider doing so? The newsletter is only once a week, and your support means the world to me. Also, FWIW, all products mentioned are independently chosen, and some may be affiliate links. Your support is appreciated!

Just so we can all agree: The holidays are not about presents, and there isn’t a prize for giving a good gift. BUT we can also agree that there is something wildly delicious about giving a truly excellent present that the recipient is actually thrilled to get. Not the “Oh, this is so nice” that they quietly say upon opening their third copy of Malcolm Gladwell’s Talking to Strangers. No, it’s the “You’re kidding me?!?!” joyful response that we’re after, and I am here to share my tactics for making this happen (or at least upping your game from whatever state it’s in now).

Tip 1: Surveil and document.

The best gifts show that you truly know the recipient, understand their needs and wants, and have been listening to them. Accordingly, I keep a document on my phone that I use to compile notes about things my friends, family, and loved ones mention.

For example, when my sister-in-law said that her favorite workout pants were on their last leg, I made a note and surprised her with a new pair of her go-to Nike leggings that year. When my husband got back into chess and the show The Queen’s Gambit, I filed that info away and then bought him a vintage 1960s wooden Soviet chess set. When my best friend was feeling frustrated because she couldn’t find the right bag that looked professional and chic but also could hold her laptop, you bet your ass I wrote that down. And yes, I eventually found her the Proenza Schouler PS1 Backpack of her dreams at The RealReal.

I also keep a running list of excellent presents that are more evergreen and not specifically tied to a certain person. That way, I always have a vetted list of good gifts ready to go!

Tip 2: Upgrade their everyday essentials.

So you didn’t have time to surveil and document things your gift recipient might like—that’s totally fine! Another trick I like to use is to simply note the things they use on a regular basis and then upgrade one of them.

If your guy friend/boyfriend/brother is still wearing cheapo T-shirts from college, why not give them a nicer version, like Buck Mason’s Slub Classic Tee or Sunspel’s Solid Crewneck, if you really want to go for it? Also, The Great makes deeply excellent men’s sweatshirts as well; The Men’s College Sweatshirt in Varsity Grey is perfect, and you can have it custom embroidered, which I 11/10 recommend. (I love using this strategy for my girlfriends, too, and trust me when I tell you no one is ever sad about getting an xKarla Classic T-Shirt or The Great’s The Slim Tee.)

You can do this with literally anything the giftee uses on a regular basis. Are they still using a ratty robe that they’ve probably had since college? Give them a cozy upgrade. Do they complain about their grocery-store cheese grater? Surprise them with Samin Nosrat’s favorite Microplane.

Or you can do something truly unhinged, like I did last Christmas, when I decided to update all of the bath and body products in my parents’ house as part of their present. It was particularly fun for me because I knew they weren’t loyal to or even cared much about the things they were currently using. I filled a big basket with carefully selected soap, shampoo and conditioner, face and body lotion, you name it, so that they’d have cleaner, more efficacious options than the random stuff they were using.

Anyway, you see where I’m going with this: Anything can be upgraded! And just to be clear, upgraded doesn’t always mean more expensive. Think about what “better” means to you—Local? Sustainable? Small-batch? Organic? More thoughtfully produced? Vetted by someone you respect?—and go from there.

Tip 3: Spoil them with small splurges.

This tip is somewhat related to the previous one but generally less practical. Basically, you’re going to want to think of the type of present that the recipient would love but would never buy for themselves.

For example, one of the best and funniest gifts I ever received was a Gucci condom case—a Tom Ford–era design, no surprise—given to me by my best friend as a college graduation/birthday/Christmas combo present. Still, to this day, it is one of the most iconic gifts I have ever received.

While that was obviously extremely fancy, a small splurge doesn’t have to be. A vintage or first-edition book sounds pricey, but if it’s something that’s more of a cult classic, the prices are usually pretty reasonable. For example, there’s a first-edition copy of the iconic The Best of Everything by Rona Jaffe on AbeBooks right now for $45. IYKYK.

Another go-to splurge gift for me is Klur’s Elements of Comfort Botanical Body Oil. The brand’s backstory is incredible—I interviewed the founder/CEO, Lesley Thornton, for my podcast Second Life and just adore her—and this oil is truly marvelous. It feels like a dream, smells like something Tom Ford would approve of, and gives your skin the most luxurious gleam.

Other things folks wouldn’t mind getting: the dreamiest socks, a candle from cult-favorite brand Loewe, pretty much any Olive & June nail polish (its best-selling cherry-red CV is a favorite), a subscription to the world’s greatest monthly book club for kids, the best lip plumper that TikTok is obsessed with, Jenna Lyons’s three favorite Loveseen faux lashes in a kit, a chic electric whisk and delicious turmeric latte kit for your wellness lover, handcrafted baby boots for the new parent in your life, an Hermès lipstick (I love Rouge Orange, but they’re all stunning), artisanal CBD gumdrops from Lord Jones (which is the Hermès of the CBD world) or the brand’s amazing CBD body lotion in its signature scent, tiny dishes from Year & Day (I have them by my bed and next to sinks to hold my rings), or the chicest award-winning personal massager ever.

Do you have any great gift ideas or strategies? I’m all ears (and I’m sure other folks would love to be inspired by your gift suggestions) and would very much appreciate it if you’d leave a comment below!

As always, thank you for being here, and thank you for sticking around. If you have any questions or concerns, or want me to touch on any topics in particular, I’m all ears. Leave a comment on Hi Everyone’s Bulletin or DM me on Instagram—I’m @hillarykerr—my inbox is always open!

xxHillary