What to wear during the holiday season is always a tricky one. Do we want to shop for alluring looks to wear at our office parties to look like a smoke show for our dreamy Italian coworker (okay, I am referencing Love Actually), or do we invest in more conservative pieces because our aunts and uncles present at most of our family gatherings won’t appreciate our most trend-forward buys? I always struggle with how to get dressed up for all the holiday events on my calendar because there is a large part of me that is torn between looking super chic versus feeling at my most comfortable. Throw in the added challenge that we are still living in tricky times, and we definitely want to make this upcoming holiday season a special one.
From curve-hugging dresses to luxe velvet pieces to comfy sets, I have all my favorite outfits listed below for whatever event you have coming your way. Even if your grand holiday plans include spending it on your own in front of the TV with your cat and a bottle of wine. Whatever the occasion calls for, I have you covered. Keep reading to see all the outfits I have planned for fancier parties, lounge-at-home days, and everything in between.
The Event: The Office Holiday Party
Now if you do have a little black number that you have just been dying to wear for the holidays, this is your sign. No potentially judgy family members present (and possibly some foxy colleagues if your life mirrors Laura Linney’s character) means that you can mind your business and focus on having fun. The outfits that are perfect for an event like this are the ones I always see glamorized in my social media feeds that I always wish I could wear but sometimes prove too impractical for family gatherings. Yep, this is your moment to shine.
I love this classic take on the Little Black Dress. This one from Norma Kamali felt amazing on and was so comfy while also being curve-hugging in all the right places. It is the ideal choice for a long and wild night out, ideally with Christmas-themed karaoke.
With any Little Black Dress, we need a statement pair of heels. These sparkly numbers add a little of that holiday flair and are ready for dancing to Michael Bublé’s Christmas soundtrack.
A sequin bag is always a winner, but this piece from Cult Gaia is stunningly luxe and sure to move with you throughout all of your holiday-season events.
Not fully on board with a dress? Pair this pretty top with a velvet pair of pants and you are ready for a long night of well-earned frolicking.
Signature headbands are the most wonderful addition to any simple outfit. This gold and glittery piece is sure to turn heads.
The Event: Christmas Eve
For many of us, Christmas Eve is one spent with our families and oftentimes our friends. This night has all the sparkle and magic of the entire holiday season rolled up into one. It’s important that we dress tastefully but also feel free to honor the festive feel of the evening. That’s why I selected outfits that are buttoned up, chic, and will give the impression that you are the most responsible child in the entire world who definitely has their shit together (in front of your family, at least).
What do you get when you mix all of the classic holiday trends together? This green velvet dress, which will look right at home next to my Christmas tree.
It’s the worst feeling being uncomfortable on our feet throughout our holiday parties. We want to look cute but feel comfortable. That’s why these Loeffler Randall heels are perfect. They feel like clouds on my feet while also looking ready to hop on the dance floor.
A jumpsuit might be just the ticket for those who are focused more on cooking the feast than getting dressed up. This DVF number is an easy and timeless choice featuring silk and velvet embellishments. Probably grandma-approved as well.
This piece is perfect for a romantic Christmas Eve.
Velvet tends to get the most hype, but silk pieces are just as dressed up and tend to be the most photogenic of all fabrics (ICYWW).
You cannot go wrong with gold accessories on any holiday, but especially on Christmas Eve.
The Event: Christmas Day
Christmas Day is a time for getting comfortable. Playing songs by the fire with friends and family, maybe even playing games all day after opening presents. This is a day for comfort and leftovers. That’s why I selected these pieces to help provide you with the most joyous day of the year with ample stomach room, even if you can’t wait to not be in the same house as your family.
A chunky knit sweater is so cozy for this day. The red color is also festive, but you can wear it again post-holidays, too.
Yep, the Uggs from my high school days are still in rotation (I’ve since updated the exact pair since), and it feels so retro to wear them again now. I’m happy they’ve made a comeback since nothing will ever top how cozy they are.
These Tkees lounge pieces are super comfy and come ready to pair in matching sets that look like a completed look. This red set is the perfect addition to any kind of Christmas Day look.
This soft set is perfect for a day spent playing card games and watching a movie marathon.
Shop the matching Nico Cropped Tank ($85).
Paired with a cute flannel or PJ set, this red beanie is giving me straight-up Home Alone vibes.
The Event: New Years Eve
Yes, this night features mostly overpriced parties. Yes, it is often a letdown. Yes, I often have to go home early because my feet hurt in way-too-tall heels. But still! This isn’t the night to let the ball drop on our outfits. After the last two years, we all need to cut loose and have some fun anyway, so let’s dress the part.
I love velvet pants any time of year, but for some reason, they feel like such a fit on NYE. They’re easy to dance in and warm enough to protect from the winter’s chill.
Glittery earrings are a must this holiday season, and these ones are the perfect addition when watching the NYE fireworks.
I am so in love with this extremely statement top by For Love and Lemons. It is highly impractical but oh-so-cute, and wearing it would make my New Year’s Eve one to remember.
Sequins are a tried-and-true NYE look for good reason. Don’t fix it if it ain’t broken.
If you get cold easily and still want to honor the bedazzled vibe of the night, opt for this standout top from 7 for All Mankind.
Up next, see which five things I stopped wearing when I moved from NYC to Texas.
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