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Classic Christmas Outfits to Wear to a Holiday Gathering

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It’s that time of year! The holidays are right around the corner, and we couldn’t be more excited to get cozier as the weather gets colder. With plenty of holiday gatherings and parties planned throughout the festive months ahead, you may be thinking about what you’re going to wear to stay warm and look stylish at each event.

We have outlined some outfit ideas to get you inspired this year. Now is the perfect time to think about warming up in fuzzy boutique sweaters, plush leggings, and other cozy clothes that can be dressed up or down depending on the occasion. At Jenny Boston Boutique, we have all the cold weather apparel and accessories you could need, so you don’t have to fret about what to wear for the holidays. Keep reading to see which classic Christmas outfits we picked!


As soon as the weather starts showing the first signs of cooling down each fall season, we are always eager to start wearing sweaters again. Whether turtleneck or cowl neck, fitted or oversized, cardigan or hoodie, we love every variety there is.

This year, we recommend options that are perfectly oversized without being too baggy or ill-fitting. Paired with jeans or leggings, this style makes for a cute and cozy look to wear at a holiday brunch.






When it comes to cold-weather dressing, you can’t forget about vests. These are extremely versatile because you can add as many layers under them as you’re comfortable with, from thin, long-sleeved tops to heavier sweatshirts.

One of our favorite styles features a little added extra, like a classy faux leather trim or soft and fluffy padding. These are perfect for walking around the neighborhood enjoying the Christmas lights or for staying warmer when you go indoors. For a dressier occasion, such as the office Christmas party, choose a drape-style vest in winter’s most popular colors: deep green, light blue, or even tan. These look chic with pencil skirts and dress slacks!


Ponchos are another great way to stay warm this winter, offering unparalleled comfort and coziness while still upholding your sense of fashion. Less restricting than jackets yet still able to keep you warm, ponchos are the wardrobe item you may have never known you needed!

Red and green tartan patterns make for a classic holiday outfit that can be worn while unwrapping presents and eating delicious food with family and friends. It can be worn with long- or short-sleeved tops and pairs well with both jeans and leggings.





While you may be thinking that it’s too cold for dresses, we are here to tell you that is not necessarily the case, as long as you style them correctly and add lots of layers.

We would choose to wear a furry vest over top of a maxi and tall boots underneath, or opt for a shorter dress paired with a leather jacket and warm scarf. You could even put a turtleneck sweater on top of yours to create the look of a sweater-and-skirt combo. No one would know the difference!

Whether going to Christmas dinner with family or attending Midnight Mass, a dress with extra layers is always a fabulous and stylish option.


Scarves are the perfect way to stay warm when you want to wear some lighter layers, so they’re a great option for when you’re going to be spending a lot of time indoors at holiday gatherings. Or, go ahead and pair yours with a chunky sweater while outside, and then take your scarf off once you’re inside if you end up getting too hot. Try an infinity scarf, classic wrap scarf, or a chunky blanket style. You can even match the colors to the rest of your ensemble for seamless accessorizing!






As much as we love jeans, leggings are truly what get us by during the colder winter months. Whenever we want to be comfy and cozy, we opt for high-rise, fleece leggings because, not only will the material keep you warm, but the waistband is super thick and constructed so that it will never roll down. Trust us when we say that these are the perfect leggings for both lounging around at home and attending holiday gatherings. They can easily be dressed up when worn with a long tunic and cardigan or boots and an oversized, chunky knit sweater, which is quite possibly our favorite classic holiday outfit idea! There’s no better combination than comfort and style.

What do you plan to wear for your holiday gatherings? We hope you were inspired by these ideas and would love to know what pieces you’re loving for the holiday season this year. Let us know in the comments what outfits you can’t wait to wear, and stop by our online store for pieces you can add to your wardrobe at great prices!


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