How to give thoughtful gifts: the single most important rule, plus seven more no-fail tips

A big bag of wooden clothespins may have been one of the best gifts I have ever received. The clothespins came from my Granny, and I admittedly laughed when I opened the package. Clothespins? Okay. She arched an eyebrow and said, "You'll see."

As time rolled by, I did see. I found myself reaching for those clothespins a million times—to close a bag of chips, hold delicate laundry onto a drying rack, pin back a curtain to patch the wall behind it. I used clothespins to gather tax documents and to clip outgoing mail to our mailbox. Clothespins held flower arrangements together in vases, became the foundation of endless crafty projects, and, as Christmas neared again, we even made ornaments from them. Granny knew how to give a thoughtful gift.

How to give thoughtful gifts

What makes a great gift? Not a perfect gift—because perfection is both rare and fleeting and thus usually not worth the trouble—but a great gift. I may be in the minority, but I looooove the task of choosing gifts. We have a large extended family with seemingly constant birthdays, holidays, and milestone events and I love brainstorming the seemingly constant gift ideas required. But I know gift-giving sometimes causes others stress—we want to get gifts just right and can feel lost in the possibilities.

I'm here to offer one simple principle that will help you choose great gifts almost every time: Pay attention. That's it.

Pay attention to what your loved ones say and do, what they notice and what they need. Pay attention to their daily routines and habits. Pay attention to their sacrifices and what they rarely do for themselves. This practice will not only offer a font of gift ideas, but more importantly—so much more importantly—all that paying attention will deepen and widen and refine your love for them.

Along with paying attention, here are seven more strategies to help you choose great, thoughtful gifts.

P.S. Through November and December I will be sharing gift idea guides for men, women, babies and kids, teens and young adults, family and friends, last-minute gifts, and even a guide to zero-cost gifts. I'm so excited for you to see them! Come back and save these posts for all your gift idea needs throughout the year. Between these roundups and the tips described here, you will be poised to give great, personal gifts ideas to those you love.

1. Give a lot of something they love.

When I say a lot, I mean a lot. Pay attention to what specific brand and flavor treats they enjoy—chips, chocolate, cookies, candy, coffee, etc.—and give a huge stash of it. One memorable thoughtful gift was the time I received a massive supply of my preferred Lily's chocolate. I occasionally buy these for myself one at a time, but having such abundance made me feel like a celebrity.

2. Upgrade something ratty that they're making do with.

Pay attention: what are they using that is technically functional but gnarly or mismatched? Their towels or drinking glasses? Give a fresh restock of pretty towels (we have bought these multiple times) or a big set of all-purpose French bistro glasses. (You could also give a mix of sizes). Their undies, socks, or pajamas? Give a dozen upgraded pairs of high quality undies, a stock of merino socks (my favorites), or a new set of matching pajamas. Are they mixing pancake batter in a random old margarine tub? Give them a proper pancake batter mixing bowl. Is their shower curtain old and faded? Give a beautiful new one paired with a set of fresh liners, because those are probably ratty, too, and then they'll have a few backups for the coming year. You get the idea!

3. Give a basic they need, but a premium version that they wouldn't buy themselves.

A beautiful electric kettle, beautiful and useful tools, next-level ear plugs, a weighted eye mask for better sleep, organic sheets, luxe body wash (or this set), a premium skincare or makeup item, really good sleeping pillows (we have loved these). Pay attention to what they need and would likely buy for themselves, and then give the leveled-up version that they may pick up to admire but put back on the shelf to be "responsible."

4. Give something that makes their daily life less annoying or solves a minor problem once and for all.

We're not just going for "easier" because we don't actually want work to be easy; we want it to be meaningful. Relieving annoyance or solving little problems allows time to be spent on more meaningful work. This silicone scrubber ended the annoying problem of disintegrating shower poufs. This tub/sink shroom actually works to catch hair. A rechargeable electric lighter solves the perpetual annoyance of not having a working lighter or matches handy when you need them. Here's the last travel umbrella you'll buy. A great rechargeable wine bottle opener. No show, no slip socks that... don't slip. A smoothly operating folding wagon you won't have to wrestle every. single. time. Nerd wax to stop your glasses from sliding down your nose. A phone grip that gives you security and mini tripod action without bulk or breaking off immediately. A flexible device holder that packs flat, smoothie bombs, a sweat liner to end ruined baseball caps, this sweater stone to remove pilling and just be done with it. Many years ago I gave Colin a huge stash of coffee shop-style paper hot cups with lids because he was constantly misplacing and losing his travel mugs, which not only lead to repeated annoyance (early in the morning) but also created mild stress over a cycle of losing stuff. When you pay attention, you'll think of so many other ways to give the gift of solution and the freedom that it brings.

5. Give a high quality kitchen tool plus a partner item.

Why specifically a kitchen tool? Living arrangements and preferences vary so wildly, but everyone eats. Giving a high-quality tool makes snack and meal prep surprisingly more pleasant. In general, upgrading anything you often touch has a remarkable impact upon your daily tasks. To make this gift special, pair the tool with a partner. At our apartment, we have this tiny but amazing knife set (pair with a basket of fresh apples or veggies, if that's their thing, or great cheese, or a beautiful steak). This is the classic Lambo of ice cream scoops; partner with some high-end ice cream. You'll be shocked what a difference a high-quality pizza cutter makes, (we also have and love this one for thin crust); pair with some really good pizza sauce. I've gifted this gorgeous teak spatula set several times—it's also great for serving salad (partner: a dozen farm fresh eggs or stir-fry ingredients).

6. Give something that improves, upgrades, or advances their leisure or passion.

Pay attention: what do they love to do when they can do whatever they want? Gift something that makes this activity even nicer. Are they beach people? Give a set of pretty beach lounge chairs: or a high-quality sun shelter. Are they organization-minded? Give a set of stylish, well-made tool pouches. Do they love playing guitar? Give a handsome gig bag. A master of the grill or oven may love this apron. A coffee connoisseur may love this beautiful French press (it comes in seven gorgeous colors). When you pay attention, you'll think of a million other wonderful gift ideas.

7. Give something with the sole function of delighting. 

Gifts are an opportunity to celebrate the pure delight of being alive, totally apart from all practicality. Pay attention to what gives your loved one completely gratuitous delight and give something that they don't need at all, something totally unnecessary, something that exists solely to delight the senses and imagination. Pretty earrings, fan gear for their favorite sports team (or fan-related decor!), a gorgeous cookbook (this one is also beautiful), a ceramic dog dish, adorable mushroom candles that you never burn (or these chic tapers), cashmere socks. Recently I even gave someone a bundle of hyper-specific plastic spoons, because I noticed that she always raves about these exact spoons at the local ice cream shop. Necessary? Nope. Just pure fun.

More gift guides coming this season

Maybe you're beginning to understand why I absolutely love gift shopping. It's a chance to connect with the heart of someone you love. Through November and December I'll be sharing gift idea guides for men, women, babies and kids, teens and young adults, family and friends, last-minute gifts, and even a guide to zero-cost gifts. Gift giving is one my favorite topics, so I'm excited to share tons of gift content to help you give great, thoughtful gifts to those you love. Bookmark this post and come back for all your gift idea needs throughout the year.

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