The holidays are here - our favorite party season! With all that fun can come a lot of questions. The holiday party invitation arrives, and suddenly we’re getting asked: What should I wear? What do I bring? How long should I stay? What do I say to someone I’ve never met? And what exactly is the right thing to do when the invitation leaves a few details up in the air?
These are the kinds of questions we hear all the time, from friends, readers, clients and the like. So, with the holiday season approaching, we decided to put together a little playbook based on the questions that come up most often, combining our two perspectives.
We believe that showing up well starts with how you present yourself, and what you wear is an important part of that. The right outfit can set the tone, but how you carry yourself matters just as much. It’s knowing how to navigate the room, make people feel comfortable, be a gracious guest and, most importantly, enjoy yourself.
Consider this your guide to what to wear, what to say and how to show up all season long.
START WITH THE INVITATION
Leslie: Before you even think about the outfit, read the invitation. The dress code is your starting point. “Festive,” “cocktail,” “black tie” and “casual” all call for something different.
And if you aren't sure what the dress code actually means, ask! There is absolutely no shame in sending the host a quick text to clarify. It is much better than arriving and realizing you are overdressed or underdressed.
One of my biggest rules when it comes to invitations: don't make assumptions. If it doesn't say “and guest,” don't bring one. If children aren't mentioned, don't assume they're included. When in doubt, ask the host rather than putting them in an uncomfortable position at the door.
Tanya: Before you even think about the outfit, start with the invitation. The dress code is your first clue: “festive,” “cocktail,” “black tie” and “casual” all call for something different. From there, think about where you’re going, who will be there and what you’ll actually be doing.
A holiday dinner at someone’s home is very different from an office party or a formal event. If the dress code feels vague, let the venue and time of day guide you, and when in doubt, like Leslie mentioned, don’t be afraid to ask the host.
Once you understand the setting, you can make the look your own. Holiday dressing can be red, green and sparkly, but it doesn’t have to be. Black, chocolate brown, winter white, burgundy, navy or even denim can feel just as festive with the right texture, accessories or styling. The goal is to feel appropriate for the occasion without losing your personal style.
DRESS TO FEEL GOOD
Tanya: The best outfit is one that makes you feel good the minute you put it on. That might be a great pair of trousers with a silk blouse and statement earrings, a simple black dress with a beautiful blazer, or dark denim with a festive top and a great heel. If you love skirts, try a metallic or satin midi with a fitted knit.
Before buying something new, shop your closet first and look at what you already own in a different way. Sometimes accessories can do most of the work, a metallic bag, velvet shoe, great belt or bold necklace can take something you already have from everyday to holiday.
Comfort matters too, especially when you’re standing, eating and socializing for hours. Think about the whole night: Can you sit comfortably? Walk in the shoes? Will you be too hot or cold? Try on the entire look beforehand, including your shoes, undergarments and outer layer, so there are no surprises when you’re getting ready. Choose pieces that fit well, let you move comfortably and still feel like you. When you feel good in what you’re wearing, it shows.
Leslie: This is an etiquette issue too! If you're uncomfortable, you won't be fully present. And being present is one of the greatest gifts you can give your host.
So yes, wear the fabulous pencil skirt. Put on the earrings you've been saving. But make sure you can actually move, eat, sit and enjoy yourself.
THE HOSTESS GIFT
Leslie: If you're heading to someone's home, I always suggest bringing a little something for the host. A candle, flowers, wine, specialty food or another thoughtful gift is always a nice gesture.
The key is to remember that a hostess gift is a gift. Don't expect the host to open the wine immediately or put your flowers on the table. They're busy making sure everyone else has a drink.
And if you're bringing flowers, even better if they're already arranged in a vase. Anything you can do to make your host's life easier is always appreciated. Here are some of my favorite hostess gifts for the holiday season: Frasier Fir candles paired with fancy long match sticks, festive cocktail napkins, a box of elegant chocolates, and a bottle of your host's favorite beverage of choice.
Tanya: I think a hostess gift is a nice opportunity to be thoughtful without overthinking it. It doesn’t have to be expensive; something personal, or simply something you know the host will enjoy, goes a long way. I usually gravitate toward a special bottle, something they might not necessarily buy for themselves or that would be a nice addition to what they already have. It feels thoughtful, easy and doesn’t create extra work for the host.
THE ART OF THE CONVERSATION
Tanya: Fashion can be a great conversation starter, especially during the holidays. A genuine compliment on someone’s shoes, jewelry, coat or the way they styled something can instantly make a conversation feel more natural.
If you’re curious, ask where a piece is from, if it’s vintage or if there’s a story behind it. And when giving a compliment, focus on the choice: “I love how you styled that” or “Those earrings are amazing” always works. Style is personal, and the best fashion conversations are the ones that make someone feel noticed, not scrutinized.
Leslie: This is where people can tend to overthink things. You don’t need to walk into a holiday party ready with a list of conversation starters.
Start simple. “How do you know the host?” is a universal opener. You can also ask about someone's holiday plans or what they've been up to lately.
And then listen. Really listen. A great conversationalist makes the other person feel interesting. Pay attention to the little things they say that spark a connection, and pick up on those threads. Before you know it, the conversation will flow naturally from there.
Ask questions, follow up and put your phone away. And if you have an Apple Watch, consider leaving it at home. Checking it every time it buzzes or vibrates can make you appear distracted, uninterested and a little rude.
THE PLUS-ONE
Leslie: If your invitation doesn't include a guest, don't assume you can bring one. If you want to clarify, a simple, “I wanted to check whether the invitation includes a guest” is appropriate.
And if you are bringing someone, give them some context before you arrive. Tell them who the host is, what the occasion is and who they might know. Walking into a room full of strangers is more comfortable when you have a little information.
Tanya: If you’re bringing a plus-one, make sure you’re both on the same page about the dress code before you leave the house. You don’t need to match (unless you want to), but your looks should feel like they belong at the same event. If one person is in cocktail attire and the other looks ready for a casual dinner, it can feel a little off.
I like the idea of coordinating rather than matching, think of a similar level of formality, complementary colors or simply making sure the overall vibe works together. You should each still look like yourselves, just like you planned to arrive together.
FROM ONE EVENT TO THE NEXT
Tanya: During the holidays, it’s common to have more than one event in a day, or to go straight from work to a holiday party, and you don’t always have time for a full change. The trick is to think about the second event when you’re getting dressed for the first.
Instead of packing another outfit, bring a few pieces that can change the mood of what you’re already wearing. Swap your work tote for a smaller evening bag, change your shoes, remove a daytime layer, add a belt or statement jewelry, and freshen up your makeup with a bolder lip if you want. You can even change how you wear something; unbutton a blouse a little, roll a sleeve or take off the jacket you wore to work. A few small changes can make the same look feel completely different without starting over.
WHEN IT'S TIME TO GO
Leslie: One of the hardest questions of party etiquette is knowing when to leave.
For a cocktail party, an hour or two can be perfectly appropriate. For a dinner party, stay through the meal unless you have a legitimate reason to leave early.
And don't disappear without saying goodbye to your host. You don't need to make a grand announcement, but find them, thank them and let them know you enjoyed yourself.
IF YOU'RE THE HOST
Leslie: If you're hosting, remember that your guests aren't coming to inspect your house. They're coming to see you.
You don't need a perfect home 1or an extravagant menu. Make people feel welcome. Put the music on, light the candles, set the mood. And, most importantly, get out of the kitchen and enjoy your own party!
Your guests may not remember every detail of the evening, but they will remember how you made them feel.
Tanya: If you’re the host, remember that you set the tone. What you wear helps establish the mood of the evening, whether you’re having a relaxed dinner with friends or a more dressed-up holiday party. This is also the perfect opportunity to wear something special you’ve been saving; a beautiful dress, a favorite statement piece or something that simply makes the night feel like an occasion.
At the same time, think about what hosting actually involves. You’ll be greeting guests, moving around, serving, sitting and probably making a few trips back to the kitchen, so choose something you can feel good in for the entire evening. You want to look festive and feel special, but not be distracted by your outfit. Most importantly, wear something that lets you relax and enjoy the party too.
SETTING THE STAGE
Tanya: I think of setting a table the same way I think about putting together an outfit. Start with a good base, then layer in the pieces that give it personality. That could be beautiful linens, interesting glassware, candles, flowers or a mix of pieces you already own.
It doesn’t all have to match, in fact, I usually prefer when it doesn’t. Repeating a color, texture or material a few times is enough to make everything feel pulled together. And just like with fashion, choose one or two things to make the statement rather than having everything compete for attention. The goal is for the table and the room to feel special, but still relaxed enough that people want to sit down, stay awhile and enjoy themselves.
Leslie: And once you've made the table beautiful, there's one more detail that can make a big difference: where everyone sits.
One of the easiest ways to take the guesswork out of the seating arrangement is to use place cards. I think they can be one of the most thoughtful touches at a dinner party.
As the host, you know your guests. Maybe you have a feeling that two people who have never met actually have a lot in common. Maybe they work in similar fields, share an interest or simply have personalities you think would click. Give them the opportunity to discover that connection by thoughtfully placing them next to each other.
And don't be afraid to mix things up! Couples don't always need to sit together, and your bestie doesn't need to be seated next to you. Part of being a host is creating an environment where your guests can meet someone new, discover a shared connection and leave the table knowing someone they didn't know when they arrived.
OUR GOLDEN RULE
Leslie: Good party etiquette comes down to consideration. Think about the host and the other guests.
Introduce yourself to someone new. If you spot someone standing alone by the cheese board, bring them into your conversation. We've all been that person... and we all remember who rescued us.
A thoughtful introduction helps too. "This is Sarah, she just got back from Bermuda" gives two people something to talk about. And before you leave, find the host and say thank you.
Tanya: My golden rule for holiday dressing is simple: dress for the occasion, but still look like yourself. Being the best dressed person in the room doesn’t mean wearing the loudest outfit or the latest trend. It’s usually about getting the details right: a great fit, one strong piece, the right accessories and looking polished without looking overdone.
Choose something that feels special but still feels natural on you. When you look comfortable, confident and like you didn’t try too hard, that’s usually what people notice most.
We hope this playbook makes the holiday season feel a little easier, a little more stylish and a lot more fun!
You are invited to join us! Join us on October 29 from 5:00–7:00 p.m. at Tanya Taylor in Greenwich for The Holiday Party Playbook, an evening of style, etiquette, conversation, and holiday fun. We can't wait to see you there!
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