Holiday entertaining used to be less about perfect tablescapes and more about goofy, memory-making rituals. If you are craving that vibe again, it helps to look back at the cozy chaos of ‘90s Christmas Mom energy and mix it with a few newer family traditions. Here are nine holiday entertaining traditions worth bringing back so your gatherings feel warmer, looser, and a lot more fun.
1. Matching Family Pajamas
Matching family pajamas tap straight into that ‘90s Christmas Mom instinct to turn even Christmas Eve into a full production. The old-school ritual of coordinating festive sleepwear was never just about photos, it was about signaling that the whole night was dedicated to being together. When everyone shows up in candy-cane stripes or plaid flannel, the pressure to “dress up” drops and the focus shifts to hanging out.
If you host, you can lean into this by putting “pajama dress code” right on the invite and keeping the night casual with cocoa, board games, and a simple snack spread. Guests who might feel awkward at a formal dinner often relax when they are literally in soft pants. For kids, the matching sets become a visual cue that the holidays are here, and for adults, they are a low-stakes way to be silly, which is exactly the kind of energy that makes a party memorable.
2. Cookie-Baking Marathons
Cookie-baking marathons bring back the ‘90s Christmas Mom habit of turning the kitchen into a full-day hangout. Those all-day baking sessions were part production line, part chaos, and completely social. Instead of presenting a perfect dessert tray that appeared from nowhere, you invite friends or cousins over early, hand out aprons, and let everyone roll dough, sprinkle sugar, and sneak tastes.
For entertaining, this flips guests from passive to active. People who do not know each other well can bond over decorating gingerbread or debating whether snickerdoodles beat chocolate crinkles. You can set up stations for mixing, cutting, and icing so kids and adults have jobs that match their attention spans. By the time the evening crowd arrives, your house smells like butter and cinnamon, and you have platters of cookies that everyone feels personally invested in, which makes the spread feel less like catering and more like community.
3. VHS Movie Nights
VHS movie nights revive the ‘90s Christmas Mom tradition of curating a holiday film marathon that everyone watches together. Back then, someone stacked a pile of tapes, rewound them, and planned the order of the night, turning a simple watch party into an event. Recreating that vibe now is less about actual VCRs and more about copying the intentional, Start style of planning a lineup that builds anticipation.
You can ask guests ahead of time for their must-watch holiday movies, then “program” the night like a mini festival, complete with a printed schedule on the fridge. Dim the lights, pass out popcorn in big bowls, and encourage people to talk over the familiar scenes instead of shushing them. That shared nostalgia, whether it is for animated classics or ‘90s rom-coms, gives different generations a common language and turns your living room into a low-key theater where nobody cares if kids wander in and out.
4. Handmade Card Crafting
Handmade card crafting brings back the ‘90s Christmas Mom habit of sitting everyone down at the table with cardstock, stickers, and glitter. The older tradition of exclusive advent-style prep was about slowing the season down with small, hands-on moments, and DIY cards fit that same spirit. Instead of ordering a glossy photo card, you invite guests to make their own mini masterpieces during the party.
Set up a crafting corner with stamps, washi tape, and pre-folded blanks, and encourage people to create thank-you notes, place cards, or greetings for relatives who could not attend. Kids can draw lopsided trees while adults write short, specific messages that feel more meaningful than a mass email. The stakes are low, but the impact is big, because guests leave with something tangible they made themselves, and you get a room full of conversation that is not just small talk about work and weather.
5. Neighborhood Caroling Walks
Neighborhood caroling walks channel the ‘90s Christmas Mom energy of organizing door-to-door outings that pulled the whole block into the celebration. The tradition of Make Christmas DIY moments outside the house reminds you that entertaining does not have to stay locked inside your living room. When you gather friends, print a few lyric sheets, and head out into the cold, you turn your party into a moving event.
Even if your group is more enthusiastic than in tune, neighbors usually light up when they open the door to live music and a plate of cookies. You can keep the walk short, hitting just a few houses where you know people will appreciate it, then circle back for hot drinks. For kids, it is a rare chance to see adults being unabashedly dorky in public, and for older neighbors, it can be the most personal contact they get all season, which quietly raises the stakes of your gathering from “fun night” to “real connection.”
6. Gratitude Jar Fillings
A gratitude jar turns your holiday party into a moment of reflection without making it heavy. The idea of collecting thankful notes during family gatherings is simple: you set out slips of paper and pens, ask guests to jot down something they are grateful for, and drop them into a jar. You can read a few aloud later or save them for a quieter moment.
As an entertaining tradition, this works because it gives everyone, from chatty teens to quiet grandparents, an equal voice. People who might not speak up in a big group still get to contribute something meaningful. You also create a time capsule of the year’s small wins and big milestones that you can revisit next season. In a culture that often treats holiday parties as content for social media, pausing to name what actually matters helps anchor the night in something deeper than the menu.
7. Shared Advent Calendars
Shared advent calendars take a solo countdown and turn it into a group experience. The practice of decorating a calendar and opening DIY daily surprises has evolved into a way to build small rituals into every day of December. When you bring that into your entertaining, you give guests a reason to keep connecting beyond a single party.
You might host a kickoff brunch where everyone helps fill a communal calendar with tiny notes, activities, or treats, then rotate who opens each day on a group text or video chat. For families who are spread out, this becomes a low-effort way to stay in sync. At in-person gatherings, you can open that day’s door together as a mini ceremony before dessert. The stakes are tiny, but the repetition creates a shared storyline that runs through the whole season instead of stopping when the dishes are done.
8. Storytelling Potlucks
Storytelling potlucks combine two of the most reliable holiday crowd-pleasers: food and good stories. The idea of sharing holiday tales over dishes at a Create Holiday Traditions style gathering turns dinner into something more intentional. You ask each guest to bring a dish that connects to a memory, then give them a few minutes to tell the story behind it when they set it on the table.
Maybe someone talks about their grandmother’s tamales or the boxed brownie mix they survived college on. Those details reveal more about people than small talk ever will, and they give everyone easy conversation starters for the rest of the night. It also takes pressure off you as the host, because the emotional weight of the evening is shared. Instead of you trying to manufacture meaning, the stories naturally surface what matters to your group, from family history to chosen-family traditions.
9. Personalized Ornament Workshops
Personalized ornament workshops turn your holiday party into a mini maker studio. The tradition of crafting unique keepsakes as party favors shows up again and again in modern holiday guides for a reason: people love leaving with something they actually helped create. You can set out clear glass balls, paint pens, ribbon, and date stickers so guests can design ornaments that mark this specific year together.
For kids, this becomes an annual series, where they can look back at their wobbly handwriting from earlier seasons. Adults might write inside jokes, favorite song lyrics, or simple initials. The stakes are low, but every ornament that ends up on a tree or mantle in future years quietly advertises your gathering as a place where real memories get made. Over time, those little objects become proof that your holiday entertaining is not just about one night, it is about a tradition that keeps growing.
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