25 Stylish Holiday Gifts for the Biggest Stumpers on Your List

Rule number one: You can’t out-cool a cool teen, so don’t even try. What you can do is give her gifts that feel like a luxe upgrade to her essentials. Think: her first pair of grown-up earrings — these LAGOS Gemstone Studs featuring a bezel-cut topaz are a striking alternative to the tiny hoops all her friends are wearing. Or a pair of plush, cozy Cloud Socks — the fashion world’s current-favorite “It sock” (yes, there really is such a thing). If she’s wearing out her leggings in 2020, this sleek, dance-inspired unitard is the one all the cool millennials are wearing (we’re trying to make that a thing).

1. Girlfriend Collective Unitard, $88, Nordstrom. 2. Brother Vellies Cloud Sock in Lavender, $35 at Brother Vellies. 3. LAGOS Caviar Color Gemstone Stud Earrings in Blue Topaz, $395 at LAGOS. 4. Lex Pott Twist Duo Standing Taper Candle, $40 at Urban Outfitters. 5. Fujifilm Instax Mini 11 Instant Camera, $60, Target.

Several readers told us they’re stumped by their parents, in particular one pair who insist every year that they don’t need gifts, and who don’t like decorative items that “just sit.” In this case, your options are twofold: Look for stylish, yet practical items that support a hobby — like a high-quality chef’s knife or low-maintenance indoor garden. Or, you can break through the wall of resistance by gifting something blatantly fabulous that your parents are too modest to buy themselves (but they’ll love nonetheless). A velvet weighted napping blanket, anyone? A monthly flower subscription? And if your parents are your rock — trust us, even low-key moms will be beyond thrilled to receive fancy jewelry.

1. LAGOS Caviar Spark Diamond Bracelet, $1,000 at LAGOS. 2. Bearaby Velvet Napper, $269, Bearaby. 3. UrbanStems The Seasonal Plan Subscription, $75 per delivery, UrbanStems. 4. Made In 8 Inch Chef Knife, $89, Made In. 5. Click and Grow The Smart Garden 3, $100, Click and Grow.

First of all, this reader’s best friend sounds awesome. But yes, we know the challenge of the friend whose tastes are all over the map, yet hyper cool and curated. This person brings on the gifting neurosis as you constantly think, “but does she have it already, is it lame, and is it her?” Take a deep breath, we have some ideas. If she’s a little too kooky to commit to a regular watering schedule for her beloved indoor garden, an artful self-watering planter is a lovely gift. If she already owns every crystal, how about one that slowly reveals itself as she burns a fancy candle (candles with surprises are 2020’s most delightful social media trend). If the now de rigeur mushroom lamp is a little too basic, what about this cute portable specimen in olive green, by culty Danish design house HAY? Or, combine her love for true crime and Scandi culture with a killer read that’ll please her spooky side (and will soon be a streaming series). And if all else fails, no one ever lost a friend giving skincare.

1. The Chestnut Man by Søren Sveistrup, $13.59, Harper Collins. 2. Wet Pot Self-Watering Pot, $34, MoMA Design Store. 3. HAY PC Portable Lamp, $95, HAY. 4. Herbivore Bakuchiol Serum, $54, Herbivore. 5. Wakeheart Relax Crystal Candle, $36, Wakeheart.

The bad news: there’s no curing your partner’s wanderlust for a while. The good news: you can help keep cabin fever at bay with gifts that are stylish and useful for the closer-to-home activities they’re into now, and travel-ready…uh, whenever that’s a thing again. A very highly-rated travel pillow will make some future red-eye much more restful, or can help them catch a decent desk nap now. If they’ve pivoted to hiking like the rest of the world, sport earbuds deliver great sound and a secure fit for all their outdoor jaunts. A portable projector can be used to host a movie night in the backyard now, or at some grand future camping adventure. And if they’ve become obsessed with tracking their steps like some of our friends (hey, whatever gets you through), they’ll most certainly appreciate this refined take on a smart watch strap.

1. LAGOS Smart Caviar Stainless Steel and 18K Gold Watch Bracelet, $1,900 at LAGOS. 2. Bose Sport Earbuds, $179.95, Bose. 3. Huzi Design Infinity Pillow Travel Pillow, $39, Infinity Pillow. 4. Todd Snyder Wool Cruiser Jacket in Olive, $598, Todd Snyder. 5. Anker Capsule Projector, $299, Anker.

Is she a secret heiress? Or just willing to carry a ton of revolving credit card debt to gift her nearest and dearest? Either way, it’s daunting giving to someone who gives you really fancy stuff. If your budget is small, there’s no shame in gifting little, reasonably priced luxuries, like a 100% silk eyemask, chic votive set, or a puzzle by the brand that’s made puzzles cooler than they have a right to be. If you have more to spend, stylish cookware (that’s still way cheaper than Le Creuset) will delight her. If you feel like splurging right back, we say go big — this Stacking Ring Set by LAGOS comes with colorful rings to match any mood, and is fittingly lavish for the person who has everything.

1. Boy Smells Hypernature Votive Set, $58, Boy Smells. 2. Piecework Disco Queen Puzzle, $26, Anthropologie. 3. Great Jones Dutchess, $155, Great Jones. 4. LAGOS Caviar Gold Color Switch Stacking Ring Set, $1,250 at LAGOS. 5. Brooklinen Mulberry Silk Eyemask $29 Brooklinen.