What’s Wintertaining? The New Trend That Will Revamp Your Holiday Season

Gingerbread house, floral top, winter beanie, Christmas cocktail

Photo by Corinne Brown. Source: Talbots, Getty Images, Half Baked Harvest

Did you know that people who decorate earlier for the holidays are happier? But beyond Hanukkah and Christmas, there aren’t usually a ton of opportunities for people to witness the joy and cheer that’s transformed your home during the festive season. We think it’s high time to change that, since your decorating skills and holiday spirit deserve to be marveled upon. Plus, why not revel in the wonders of winter as much as you can?

Meet “wintertaining,” a term coined by our friends at Talbots that’s about to become your new favorite. It’s the idea that you can celebrate with your friends and family anytime, not just on major holidays. There’s nothing that offers that warm, fuzzy feeling quite like dressing up, drinking some eggnog, and spending time with the people you love — and there’s no need to limit that feeling to Christmas day. That’s why we’ve come up with a unique list of fun and festive out-of-the-(gift)-box ideas for entertaining this season, complete with the perfect outfit from Talbots to mark each gleeful get-together. Trust us — your friends will thank you for giving them even more reasons to make merry, and you might even inspire them to do some wintertaining themselves.

Gingerbread House Party

Gingerbread house
Source: Getty

Why it works:

In the words of Nat King Cole, the holidays should be celebrated by kids from 1 to 92. So this season, honor your inner child by inviting pals over to decorate gingerbread houses. Whether you want to do this with couples, lady friends, or families with kids, decorating gingerbread houses is a surefire way to get anyone in the holiday spirit.

What you’ll need:

If the idea of constructing the house from scratch gives you flashbacks to a never-ending home renovation, have no fear: You can buy fairly inexpensive pre-made and undecorated gingerbread houses anywhere from Williams Sonoma to Trader Joe’s. Most of these kits come with icing and others even include candy. If you’d rather go DIY with your sweet selection, make sure to get candy that’s not too heavy and will easily stick to your masterpiece mansion: think gumdrops, life savers, and M&Ms. And of course, no gingerbread house is complete without candy canes. If these flavors aren’t your fave, we can assure you that you won’t want to eat your masterpiece when it’s finished…especially once it’s been sitting on display for a few weeks.

What to wear:

Cozy Cowlneck

Courtesy of Talbots

For some of us, making a gingerbread house is an exacting art form…but for most of us, it’s a perfectly imperfect mess. That’s why you need an outfit that’s comfortable and will allow you to move easily around the room to scope out the competition. Plus, the color of this elevated-casual dress won’t highlight any of the white icing you’re inevitably going to spill on yourself. Even more importantly, you can machine-wash it in cold water so you don’t have to worry about getting a little messy. The cable-knit texture is great for the season but will also work outside of the winter months. It’s a dress you’re going to want to wear again and again, whether you pair it with a low-heeled boot in September or a pair of warm tights in December. In fact, it’s so versatile that you’d want to steal it from a friend’s or sister’s closet immediately (And she is going to be so mad when she sees on Instagram that you wore it at your gingerbread house party.)

Cable Knit Cowl-Neck Sweater Dress

Holiday Movie Marathon

Source: Getty

Why it works: While parties are the reason for the season, sometimes you need a night to relax with friends. Remember the days when the best thing in the world was having a sleepover with your besties? Recreate that nostalgia by inviting your friends over for a holiday movie marathon. Yes, we know that holiday movies can be a bit sappy, but that’s why we love them. They make you feel like you’ve been transported into a happy little snow globe, where every ending is happy and wrapped up in a perfect Christmas bow. 

What you’ll need:

The Hallmark Channel’s viewership must increase by 1000% in November and December, because any movie lover knows it’s required viewing for the best modern holiday fare. If you’re more of a vintage movie buff, Turner Classic Movies usually offers a Christmas movie marathon starting in mid-December. Some of our all-time favorite recs are Elf, It’s a Wonderful Life, and A Christmas Carol (the Muppets version, of course.)

Make sure to keep your friends feeling merry and bright during the film with a special drink like the frosty vanilla espresso martini (one of Katie’s favorites). Of course, no movie marathon is complete without some sweet snacks, so if you’ve got time before your friends arrive, try making these mouthwatering chocolate chip cookies, or Joanna Gaines’ no-bake chocolate peanut butter balls. If you don’t have time to whip something up in the kitchen before the big night, in the words of Ina Garten, “store-bought is fine.”

What to wear:

Comfy Cashmere

Courtesy of Talbots

“Holiday movie marathon” is basically a synonym for comfy and warm, and this sweater is both. The soft fabric is perfect for snuggling up next to your favorite people on the couch. If the good vibes and crackling fire lull you into a peaceful rest, the material of this sweater will make you feel completely rested and ready for movie number three, whenever you wake up from your cat nap.

Cashmere V-Neck Pullover

Secret Santa Exchange

Friends exchanging gifts
Source: Getty Images

Why it works:

While the holidays are primarily about being thankful for what you have, there’s no denying that everyone loves gifts. We prefer a Secret Santa exchange — in which you know the identity of your recipient ahead of time — to a Yankee Swap, which can be confusing, long, and inevitably leaves someone feeling slighted. Secret Santa is a great way to put some real thought into what’ll make a friend happy, and there’s nothing like seeing the smile on a loved one’s face when they open that perfect gift.

What you’ll need:

Since it’s tough to get people together to draw names from a hat, ask someone who won’t be attending (maybe a friend who lives out of state, or a sibling who’s got other plans) to make the assignments for you. Then give them each attendee’s phone number, so they can text them the name of their giftee. Make sure to set a price limit, so nobody feels pressured to go overboard.

Since the actual opening of Secret Santa gifts only takes a few minutes, it’s a great excuse to transition to a cocktail party. Pour a holiday-themed drink (the frosted mistletoe margarita is sure to be a crowd favorite), throw on some classic tunes, and light up the tree: It’s time to get ultra-festive.

What to wear:

Stunning Suit

Woman poses in black velvet suit

Courtesy of Talbots

Most of us associate “holiday party outfit” with shiny red dresses or tartan prints and big bows. This elegant suit will completely shake things up and make everyone in the room wish they’d gone for something a bit more daring. This chic style has been worn by everyone from Julia Roberts to Victoria Beckham, so don’t be surprised if your friends mistake you for a celebrity.

The blazer is tailored for a feminine look, and the sequined top offers a fun little sparkle that’s party-ready. The black-on-black will look great in pictures and elongate your frame no matter your height, and the velvet gives an extra holiday flair. Perhaps most importantly, the color will keep you from fretting about getting a little cranberry juice on your lapel. Pair it with bright pumps for a pop of color, and every person who arrives at your door will comment on how amazing you look.

 

Winter Wonderland Walk

Friends on winter walk
Source: Getty Images

Why it works:

Sometimes, the best way to embrace the magic of the season is to take a moment to appreciate all the beauty nature has to offer. A walk or hike through the woods with a group of friends is a great way to catch up and admire the surroundings you usually overlook. Depending on whether your area has seen some snowfall, you might even find yourself in an impromptu snowball fight — this should be a day of rosy cheeks, lots of laughter, and childlike joy.

What you’ll need:

Luckily, this one is pretty easy: All you’ll need is a group of friends and possibly a car or two to reach your outdoor destination. If you’re not sure where to find a good stroll near you, AllTrails is a free app that can help you find local hikes and walking trails for adventurers of all experience levels. 

What to wear:

Functional Fashion

Woman in warm outfit standing in the snow

Courtesy of Talbots

There’s nothing worse than feeling cold and wet on a walk. That’s why we love this winter-ready outfit: The sturdy boots will keep your feet warm and dry no matter the terrain, and the adorable snowflake print is spot-on for cooler temps, without being overtly holiday-themed. The pullover and pants are stretchy enough to help you keep up on a fast-paced birdwatching walk — or any other kind. The coat will help you retain heat in case a light snow starts to fall, and the pom-pom hat is playful and cute enough to make any woman feel young at heart.