We’re officially in the midst of the holiday season, and all the plans and preparations are in full swing. Top of mind for all of our upcoming festive soirées are the looks, the menus, the cocktails, the party soundtracks, and—most importantly—the gifts. For over a decade, one of my go-tos for shopping inspiration when it comes to buying the chicest, most covetable pieces, from fashion to home décor, has been the one and only Hillary Kerr.
This is no surprise, as Kerr is one of the industry’s most sought-after players, having a hand in creating an array of impressive ventures with endless accolades to match. This includes co-founding Who What Wear, creating and hosting the ever-popular Second Life podcast, documenting all her shopping recommendations and advice on her highly followed newsletter Hi Everyone, and being an SVP overseeing a variety of publications, including Who What Wear, Marie Claire, and more. Like I said, her opinion is gold.
It’s for those reasons and many more that I was more than elated to get Kerr’s firsthand take on holiday gifting this year. Whether it’s her keen eye for standout gifts that fashion people worldwide would swoon over or her thoughtful approach to gift giving (I’m definitely going to be adopting her templatizing trick!), this guide is not to be missed. Keep scrolling to check out all of Kerr’s incredibly chic picks along with her helpful gifting strategies.
1. Personalized Gift
“There are so many amazing personalized options out there, but I’m really a big fan of personalized luggage and packing cubes from Paravel. The brand makes the chicest suitcases made from sustainably sourced materials (the bags are carbon-neutral), and they even have an airline compatibility guide so you can be sure that your carry-on size will work for the airline you travel the most.
“Even better: They offer four ways to personalize your pieces, and the results are really lovely. The Aviator Carry-On Plus in Sandstone Black or Safari Green are two chic choices (I own the former!), or if that feels like too much of a commitment, you can customize a set of their amazing packing cubes.”
2. Future Heirloom Gift
“When considering a future heirloom gift, it’s best to look for timeless pieces with universal appeal, and for me, that’s the Tiffany T1 Wide Diamond Hinged Bangle. It’s elegant, and has universal appeal, and would look phenomenal on anyone and with just about every type of personal style I can imagine.”
Paravel
Aviator Carry-On Plus
Paravel
Packing Essentials Set
Tiffany & Co.
T1 Diamond Hinged Bangle
3. Gift They Won’t Return
“My most crowd-pleasing gift is the Whipped Long-Sleeve Shirt from Negative. These T-shirts are so soft you’ll never want to take them off. They’re phenomenal for sleep, but they’re versatile and can be used for daytime dressing too. You can wear them as a super-thin layer under your favorite sweaters or short-sleeve dresses, almost like a bodysuit, but they’re also opaque enough to wear tucked into a leather skirt or high-waisted trousers for cocktails with your friends. They’re truly day-to-night in all the best ways and manage to be sleek, sexy, and cozy all at once.”
4. Unexpected Gift
“I always check out Cuyana for presents, and this year, the brand has made these delicious little bags that are perfect small presents. There’s a Pear Pouch that’s just yummy and a cherry one that’s so sweet too. They’re great little organizers to have in your bag, and they just spark joy for me. Plus, Cuyana is an incredibly thoughtful female-founded brand, and their products are super high-quality, so anything you buy is sure to please the recipient.”
5. Gift You’d Love to Receive
“Not to make this about me, but I have been thinking about the Tiffany HardWear Graduated Link Necklace for several years now, which is an excellent sign. I’m completely smitten with it, as it’s so elegant and powerful. It’s a piece I would wear for decades, adore styling with everything in my wardrobe, and then eventually share with my daughter. A truly stunning piece that will elevate anything you wear, period.”
Negative Underwear
Whipped Long Sleeve
Tiffany & Co.
Graduated Link Necklace
6. Perfectly Useful Gift
“If you have a baker in your life, I very much recommend giving them the phenomenal All-Clad Odd Size Measuring Cups and Spoons. They’re incredibly well-made, and they serve a really useful purpose, as they are all nonstandard sizes that normally require using multiple cups or spoons otherwise, like: three fourths of a cup and 1.5 tablespoons. Is it a little odd? Yes. Will they adore it? Also yes.”
7. Stylish Kids Gift
“My daughter is deeply interested in dresses, and if you’re shopping for someone like her, the splurgeworthy options at La Coqueta are outrageously lovely. We are big fans of the brand’s velvet Mary Jane slippers as well. You also can’t go wrong with personalized pajamas from Petite Plume! We love the green striped sets and get the kids’ names embroidered on the pocket, and it’s always a big hit.”
La Coqueta
Palmira Empire Dress
La Coqueta
Velvet Mary Jane Shoes
Petite Plume
Twill Pajama Set
8. Worth-It Luxury Gift
“Over the course of my life and career, I’ve had the good fortune to wear a number of incredibly standout pieces of fine jewelry, and Tiffany’s Lock Bangle is at the very top of that list. It’s hard to find phenomenal pieces that are chic and statement making, but this bracelet does both. A phenomenal gift, to be sure.”
9. Gift of a Great Read
“While I love a good coffee table book as much as the next fashion enthusiast, my go-to book gift is to buy a vintage cult classic instead. AbeBooks has a stunning assortment of options from around the world, and you can get really high-quality vintage books for excellent prices. I love to buy fashion friends first editions of Judith Krantz’s Scruples, Rona Jaffe’s The Best of Everything, or Valley of the Dolls by Jacqueline Susann, or if you’re rich and love me, I’d be happy with an original copy of Eve Babitz’s Eve’s Hollywood. This works for pretty much any category or person under the sun. Just find an author they adore, then pick a deep cut from their oeuvre, and you’re golden!”
10. Gift of Snacks and Spirits
“I’m deeply into everything from Ghia, especially the brand’s Le Fizz, which is sure to please even your snobbiest friends. The bottle is chic as heck. It’s delicious, nonalcoholic, no added sugars or artificial flavors, and the brand’s founder, Mélanie Masarin, is your favorite cool girl’s favorite cool girl. Very #IYKYK!”
Tiffany & Co.
Lock Bangle
Jacqueline Susann
Valley of the Dolls
1. Thoughtfully templatize your gifts.
“My overall best gift-gifting strategy is to find an incredible signature gift for a group of folks in my life and then just do that for everyone. For example: My best friends are all getting a session with celebrity makeup artist Joey Maalouf for the holidays. A few years ago, I gave everyone on my team at work a personalized sweatshirt from The Great. And this templatizing scheme works for non-holiday presents as well. My kids’ friends all got Super Smalls bead kits and a small Squishmallow for their birthdays this year, and that might change next year, or maybe not! Who knows. My point is that I think it’s wonderful to have a go-to gift for an assortment of the people in your life, especially if that gift is excellent. High impact, low fuss—what’s not to like?”
2. Upgrade their everyday essentials.
“As a Virgo, I’m a hugely competitive gift giver and pride myself on giving excellent presents. My favorite trick is to upgrade someone’s everyday essentials, giving them a more luxurious version of a staple they already adore, taking a key piece they love—like their go-to white T-shirt that’s seen better days or a lower-quality cashmere crewneck sweater—and giving them a leveled-up version. (I love Leset’s T-shirts, for the record.) No one is ever mad about it.
“The best part about this strategy is you can upgrade or curate options for your giftee for any part of their home or life. For example, one year, I upgraded everything in my parents’ bathroom with products that I know and love. That included shampoo and conditioner from Roz, bodywash from Necessaire, lotion from Kiehl’s, skincare from Dr. Idriss, towels from Matouk, and sunscreen from Supergoop.”
3. Spoil them with small splurges.
“Giving someone an over-the-top version of a really utilitarian product is another one of my gifting tricks. One year, I gave a few of my friends an extremely luxurious lip balm from Hermès, and the response was overwhelming. It’s the sort of thing they might not have bought for themselves but feels so fun as a present.”
4. Keep a year-round idea list.
“My true secret for giving the best gifts ever? I have a note on my phone for all my favorite people, and any time they mention something—whether it’s something they love or a pain point they’re dealing with—I add it to my file. Then when it’s time to shop for their birthday, an anniversary, or the holidays, I have a running list of ideas, which saves me from panic-shopping at the last second.”
Joey Maalouf
Makeup Session
The Great
The College Sweatshirt
Super Smalls
Alphabet DIY Bead Kit
