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Dressing for December: Christmas Outfit Inspo for Every Event on Your Calendar

By
Cassie Bird
Last Modified on November 18, 2025

This post may contain affiliate links.

The Christmas season always flies by, but luckily, there are plenty of fun things to do to make the most of it! With a little careful planning, you can fill your December calendar with a stacked winter itinerary. Sleigh rides, going to the ballet, baking cookies… there’s no shortage of fun and festive things to do when the holiday season rolls around. Whether you’re looking for holiday activities or Christmas outfit inspo to go along with it, we’re here to help!

1. Sleigh Ride

scarf coat | leggings | boots | bag | gloves | earrings

Is there anything more charming or nostalgic than a sleigh ride through the snow and pine trees? This might just be the most majestic Christmas activity. You get to enjoy the frosty air and gorgeous winter scenery, all while bundled in a blanket. All you have to do is sit back and enjoy the views!

Traipse through the woods on your vibey sleigh ride in a look that’s as comfortable as it is chic. A scarf coat is the best of both worlds. It’ll keep you plenty warm, but also looks polished and high-end. Pair it with comfortable leggings and a pair of knee-high boots – you can also try riding boots if you want to lean into the equestrian look! Then keep your hands nice and toasty in a pair of cashmere-lined gloves from Quince. Now you’re ready to enjoy the winter scenery in style (and take plenty of photos, of course).

2. The Ballet

shoes | dress | coat | bag | earrings

The holiday season might just be one of the most special times to enjoy the arts. There’s nothing like getting dressed up, going to a fancy dinner, and then enjoying a cozy evening in to watch a show or enjoy a musical performance. The great thing about these activities is that you don’t have to worry about the weather spoiling them – and if you hate the cold, an evening in a warm theatre is the perfect spot to spend a winter’s night on the weekend.

When you think of styling a look for the ballet, think classy and elegant! An off-the-shoulder black dress is the perfect piece to pull on – or your favorite LBD. Then, go for some festive accessories. Pearl-detailed heels and pearl bow earrings are a great way to get into the holiday spirit, and red lipstick is the cherry on top.

3. Vintage Train Ride

shoes | dress | coat | bag | earrings

A vintage train ride might just be the newest addition to my holiday wishlist! Just imagine cozying up in an old-school train car with vintage furniture and a warm atmosphere that takes you back to simpler days (maybe even with a fancy cocktail or mocktail in hand).

Of course, you’ll want a look that matches the old-style elegance of the train ride! If you like to dress up, channel a bit of old Hollywood glam with a faux fur coat. Underneath, a sweater dress in dark red or burgundy is ideal for a sophisticated look – even the ruffle detail at the bottom of the skirt gives off a vintage vibe. Classic accessories complete the look!

4. Orchestra Concert

skirt | dress | shoes | clutch | earrings | ring | gloves | coat

As fun as holiday parties are in the Christmas season, sometimes a night out to sit back and enjoy a performance is just the break you need from the hustle and bustle of shopping, wrapping, and cooking. And what makes your night out even more special? The opportunity to get dressed to the nines to enjoy some great music!

A symphony or orchestra performance calls for a classy, timeless outfit idea. You can never go wrong with black and white if you’re looking for the perfect color combination. And if you do want to add a pop of color, you can always do it with a red lip!

Even if your wardrobe isn’t full of black-tie ready gowns, you can get creative with the pieces you already own. For example, try creating a mixy dress from scratch by layering a satin skirt underneath a little black dress – they’ll end up looking like a designer gown. And of course, you’ll need accessories that look just as elegant. Elbow-length gloves, a long wool coat, slingback heels, and crystal details do the trick perfectly.

5. Christmas Market

boots | jeans | turtleneck | sweater | bag | coat | earrings

If you’ve ever wanted to transport yourself to Europe during the holiday season, all you have to do is attend a Christmas market! These open-air markets are especially popular in Germany, France, and other countries in Eastern Europe, but there are plenty to choose from in the United States and other places in the world as well. Go stall to stall to shop for ornate ornaments and decorations – with a cup of mulled wine or hot chocolate in hand to keep you warm.

Because these markets are open-air in the wintertime, you’ll want to bundle up! For a casual look that still feels festive, try a Fair Isle sweater and classic denim. Add a wool coat for warmth, and a pair of ankle boots. You can opt for a kitten heel or a flat version if those are more comfortable to you! Then all you need to do is add a pop of color – red is perfect for Christmas time, and a red bag and red lip are the perfect finishing touches.

6. Ice Skating

skates | jeans | socks | sweater | scarf | necklace | earrings

Heading to the rink to live out your Ice Princess dreams? (This movie is forever a classic to me!) Skate in style with a pair of straight-leg jeans, a cable knit sweater, and a plaid scarf. This is the perfect Christmastime outfit formula that will never fail you. Plus, it’s comfortable enough to move around the rink. If you need a little extra warmth before you break a sweat, just add your favorite winter coat. Simple gold jewelry completes the look!

7. A Tree Lighting

boots | leggings | coat | sweater | hat | earrings

Although Rockefeller Center might be the most famous tree lighting you’ve heard about, chances are, there might be one a little closer to home for you to attend! It’s a fun way to kick off the holiday season with your community – it’s like a Christmas party for your whole town or city.

You might be standing outside and socializing for a while if your tree lighting takes place outdoors, so make sure you start your look off with a chic coat. Underneath, go for a tonal look by reaching for a sweater in a similar color. Leggings and knee-high boots are comfortable and easy to wear on the bottom. And of course, add a cute hat for added warmth – and make sure you’re holding something hot, too, or grab some gloves and hand warmers.

8. Cookie Baking

loafers | tights | bag | skirt | sweater | earrings

Alright, for our next Christmas activity, let’s move indoors! A cookie-baking day is a fun tradition to plan each year. Whether you’re getting together with friends or family, you can all contribute a favorite recipe to bake and then spend the rest of the day decorating and sampling the result (after all, taste-testing is a crucial part of any cookie-baking day).

Indulge your sweet tooth in Christmas outfit inspo that feels just as sweet! If you love preppy outfits, you’ll love styling a tartan skirt for the holiday season. Then, on top, go for a cable knit sweater. It’s the perfect cozy style for a chilly winter’s day, plus it adds texture to your look. And if you want a little extra warmth, add a pair of sheer black tights to pair with your classic loafers. A pair of elegant, yet understated pearl stud earrings is the cherry on top!

9. Shopping for Gifts

boots | pants | sweater | bag | coat | earrings

Now, I love to shop at any point during the year, but there’s something extra magical about shopping during the holiday season. Maybe it’s because you’re browsing for the people you care most about, as is everyone else that’s out and about! Finding the perfect gift takes time and energy, but it’s all worth it to see your friends and family open their gifts with a smile on their faces.

If you’re in for a long day going from store to store, you’ll want to wear a look that’s as comfortable as it is chic! Satin or silk pants are the solution – they look elevated, but have a super soft material and an elastic waistband. On top, a cozy turtleneck and a long wool coat are great accompaniments from your winter capsule wardrobe. Add a large tote bag to help hold your gifts, and a pop of red for a Christmas-inspired touch in your lipstick. Now you’re ready to make a whole day out of holiday shopping – maybe with a nice lunch and coffee break thrown in there, too!

10. Cocktail Party

heels | dress | coat | bag | earrings

The holiday season has no shortage of Christmas parties to attend. From the office cocktail hour to a family while elephant exchange to a dinner party with friends, make sure to have a go-to outfit on hand for these types of get-togethers! It will make dressing for the holidays way less stressful.

One of my favorite places to turn to for cocktail party inspiration is French girls. After all, they know how to do a classy soirée right! To take a hint from their effortlessly chic style, go for a neutral look (with the occasional pop of red or burgundy). And don’t shy away from classic patterns – they love including leopard print in their outfits! Texture is also key – and a velvet dress perfectly fits the occasion. Keep your accessories classic with a red lip, a vintage-inspired bag, and slingback heels. If you’re feeling bold, try adding a pair of statement earrings to polish off your classy cocktail look.

Christmas Outfit Inspo You’ll Want to Save

The holiday season is almost here, and we’ll all be booked and busy in no time! To make the Christmas season a little less stressful this year, make sure to save this outfit inspo for all of your holiday events. It will make it that much easier to live in the moment and enjoy every second of it!

Is your calendar already filling up with classy party invites? Here’s what to wear! Up Next: 9 French Girl Cocktail Party Outfits Using Their Favorite Party Pieces

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2 Comments

  1. I smiled at your cookie baking outfit. As someone who bakes a lot of cookies, it’s never occurred to me to wear a plaid mini-skirt, or to have a purse nearby! Where’s the apron? But it is a cute outfit.