23 Foolproof Gift Ideas for the Pickiest People in Your Life

A small thing that sparks major joy is when a friend texts you a link to something and says, “I think you would love this.” Tap into a similar energy when gifting your best friend by writing, “I think you would love this” on a tiny note card and affixing it to the base of this heirloom-worthy brush. La Bonne Brosse specializes in gentle, smoothing, and ridiculously attractive hairbrushes. The spiraled handles are made of cellulose acetate (the same kind of material you’ll find in luxury eyewear), and the elegant oval paddle on this No. 2 brush is flanked with natural boar bristles. Your BFF will feel like an actual princess every time she brushes her hair, which is priceless, no?

The 2976 Chelsea boot stands taller in Polished Smooth leather with a Quad platform sole. Classic DM’s touches appear from heel to toe, with yellow welt stitching, a grooved sole, and a black and yellow heel loop.

If your BFF is picky, we’re assuming she doesn’t appreciate the pesky wind blowing her perfectly coiffed hair (see: above) into annoying little strands that get caught in various orifices. No worry; this lightweight babushka will envelop her ears, hair, and mug in superfine non-scratchy merino wool—ideal for unpredictable AC gusts on airplanes and crack-of-dawn walks to the gluten-free bakery. This one is in an all-at-once trendy and timeless red that makes for the perfect kind of camouflage: mysterious and attractive stranger.

“Someone special” could mean anyone, of course, but with this suggestion, we’re imagining someone who isn’t a serious significant other but maybe could be in the future? (i.e., someone you’re dating or perhaps just making out with regularly enough that they’ve made it onto your gifting list). For this person, it makes sense to gift something that feels somewhat impromptu and therefore casual (even if it wasn’t in reality), and a book you happened across while browsing at a local bookstore fits the bill. This one muses on the inextricable “twin joys” of reading and eating … and eating while reading, which perhaps is allegorical to your relationship.

Again, try to play it cool when shopping for your situationship or not-so-significant other. You definitely don’t want a present that screams, “I spent weeks looking for the perfect gift and spent all of my money on it because that’s how much I love you.” Extremely uncool behavior! Gifting matchsticks, on the other hand, feels very casual since they’re small, subtle, and affordable. We suggest these from Homesick, since the box is adorned with a phrase that will make your special someone feel seen.

You know what they say: The true test for how well you know your long-term partner is if you’re willing to risk buying them something they can’t return. Joking! But we do think there’s something kind of fun about buying clothing for a picky loved one, as it does require some degree of bravado. A necessary trait when shopping the notoriously finicky but nonetheless beloved Aimé Leon Dore.

One of the many great things about picky sisters is how they implicitly understand that whatever you get them as a gift can and should be something you’ll both be able to enjoy. Ergo, a box of Happy Menocal x Chairish stationery is just the thing — accompanied by a serious offer to be your sister’s pen pal. This stationery makes letter writing feel like eating a mini-tureen of chocolate soufflé: a gorgeous, glorious indulgence. Even the box the stationery comes in is an experience unto itself. We’re betting receiving a letter written on it feels similarly, hence the win-win nature of this exchange.

Is she not remotely offended by the proliferation of food-based monikers for beauty techniques? Lettuce speak in a language she’ll understand this holiday season(ing). The Soup du Jour of 2023 has been Hailey Bieber’s Lip Tint, a juicy gloss tinged with the color of various gastronomical delights. She’s probably wanted every flavor that’s come out, but our favorite is Toast, which the brand describes as “a hot piece of French toast.” Okay!

A Soft Services microcrystal Buffing Bar is an ideal beauty product to gift someone who isn’t really into “beauty.” It’s incredibly effective — your bro will genuinely look forward to using it, as a few Cut Shop staffers can attest — and it’s specific enough that he likely won’t already have something similar. Plus, because each one comes prepackaged in cute paper, you don’t have to go through the extra step of gift-wrapping it. (Would he notice anyway? Cries in eldest sister.)

Most gift guides for dads, if we may be so bold, are bad. (Not ours, though!) Please, we beg of you, don’t get your picky dad a pair of noise-canceling earbuds or a set of whiskey stones. Instead, get him something he’ll actually look forward to using every damn day. With this genuinely renowned machine, you’ll be gifting him the well-earned warmth of indulgence. There’s a side of nostalgia in it too, since the Dutch-made Moccamaster hasn’t updated its design since the ’70s (the machinations, on the other hand, have been finessed). Oh, and don’t forget to tell Dad that Moccamaster offers one of the best warranties in the business; it’s his love language.

Even if your dad’s style is a bit all over the place, he’ll appreciate the simplicity and functionality of this leather briefcase. The interior is spacious and expandable, while the exterior features a luggage strap and a front slip pocket for his phone or wallet. Crafted from high-quality Tuscan leather, this briefcase is made to last (plus it comes with a convenient and comfortable shoulder strap).

Another practical gift that will pair well with everything in his closet? These gloves by Todd Snyder. With premium insulation and rib-knitted cuffs, these are essential for dads who commute to work or insist on tailgating no matter what the temperature is.

Picky or not, moms are notoriously tough to gift. After all, what present could ever be good enough for the woman who once painstakingly cut the crusts off all your grilled cheeses and clipped your toenails while you slept? Perhaps … a set of linen napkins embroidered with her initials! Made-to-order monogrammed napkins are an exemplary picky-person gift idea because finding and ordering them requires the kind of effort the recipient will undoubtedly appreciate.

Gifting jewelry can be difficult if your mom is stylish yet very particular; you don’t want to gift anything that’s out of her comfort zone, but you don’t want to gift plain gold hoops either, since she probably already owns a pair. These teardrop earrings by Lele Sadoughi are the perfect happy medium.

A great gift is usually something uniquely suited to the person you’re giving it to or something specific that most people would want but probably don’t already have. By definition, an acquaintance is someone you don’t know that well, so you have to go with the latter categorization. Coasters are something pretty much everyone can use more of, especially given how much we’re supposed to be hydrating — and these gemstone ones will serve as beautiful and unique décor without being too over the top.

If you’ve got a picky boss, we hope they’re the good kind (a discerning mentor with high but fair standards) instead of the bad kind (a control freak with irrational whims). Either way, fresh seasonal fruit from Frog Hollow Farm will measure up to their exacting specifications. The legendary produce will feel intentional and somewhat fancy but not too over the top. Just make sure to order now; boxes are so popular that the farm takes preorders.

As a shopping editor, I know there is a category of products that most people are curious about but few would actually buy for themselves; these are the “nice to have” items that usually make excellent gifts for picky people. For example? Caraway cookware. The pots and pans have earned plenty of buzz over the past few years (and rightfully so!) because they’re nontoxic, nonstick, oven safe up to 550 degrees, and practically indestructible, even for people who burn everything like me.

Don’t overthink it. Which happens to be the same ethos D.S. & Durga took when crafting this distinct new scent. Originally released last year as a limited run from the Brooklyn-based perfume house, this not-just-a-gourmand comes on with nutty pistachio and spicy cardamom that’s offset with woody patchouli and a comforting creaminess. It’s the sort of crowd-pleasing scent that’ll charm just about anyone on your list.

Any coffee or tea drinker will appreciate an Ember Mug, trust me. It will keep their beverage at the ideal drinking temperature for hours, so they can leisurely sip throughout the day.