Seven Days of Holiday Outfits (Main Character Edition)

Seven festive looks I actually wore—from casual house parties to full holiday glam.

It’s my favorite time of the year—holiday shopping, festive parties, and plenty of chances to be merry (ideally with a cup of cheer in hand). As an extrovert, I thrive during this season—especially when it involves red heels and big fur.

I’m no Coco Chanel, but I can put together a killer holiday look. So instead of a full wardrobe guide, here are seven outfits I actually wore this Christmas season—for your viewing (and styling) pleasure.

1.  We kicked off the season with my own Christmas party look—I hosted a few friends at my house and then we headed to our favorite hotel bar. (The Liberty in downtown Boston, if you must know) I went classic with leather trousers from Zara and a cowl high neck sequin top that I scored on Poshmark. Luckily it only faintly smelled like cigarettes!

Hack: Poshmark, eBay, and Mercari are gold for holiday pieces you’ll only wear once. Check condition, save money, sparkle anyway.

2. The next outfit was for Siena’s Christmas party for alumni at the Saint Anthony Shrine in downtown Boston. Now despite heavy pours, this is a very classy, “keep your shit tight” event. You know the outfits you create in your head and then you’re unsure if it’ll look good on you? This was one of them! I wore a burgundy slip skirt from Old Navy (my fave- I find so many great pieces there) paired with a white sequin top from Express. Express often has some of the best holiday pieces. The quality is always there, and the styles feel elevated without trying too hard. I paired this with gold sparkle heels from Dream Pairs on Amazon—the only heels that truly fit my big ass foot. (picture down below in bottom left!)

3. Emily’s holiday party deserved a casual-but-sexy moment—and it turned into one of the best parties of my life, bar none. We had such a blast with keg beer, holiday tunes by her husband’s band, and everyone in Santa hats. Leather leggings from Old Navy, and a novelty 'Santa Baby' sweater from Cece kept it playful without feeling sloppy — perfect for a house party that turned legendary. I finished it off with black heeled booties—comfortable enough to survive the whole night.

4. My cousin’s Christmas Dinner party in Southie deserved a festive flare, and I wanted to keep it casual. I went with a Blair Ottoman below-the-knee white sweater dress from Nordstrom Rack with bright red pumps from Dream Pairs to tie the outfit together!

Hack: Red and green don’t have the be the ‘classy’ colors for holiday looks—it can also be white! A bright, fun way to pair with heels or purses.

5. After I rolled back into New York for the holidays, I immediately had a family friend’s Christmas Wassail party. A very fancy event, and boy was I ready! I wore my red sequin cardigan with black bows from Nordstrom Rack (sadly it sold out so no link for you), paired with leather pants from Zara, and my gold sparkle pumps from Dream Pairs. This felt classy, iconic, and very main character for a Wassail party.

(Purse is just a black sequin simple zip up from Amazon!)

6.  On Christmas Eve Eve, my friend Emma and I created a tradition years ago where we get drinks to celebrate together. I really hit the nail on the head with the outfit I chose for this—a simple long black sweater dress from Gap with tall black boots and an ASOS fur coat. It screamed classy and elegant.

Christmas Eve Eve drinks!

7.  The last outfit stop brings us to Christmas Eve! I wore an Eliza J black sequin (can you tell I love sequins?) dress from Nordstrom Rack with stockings and red pumps again—paired with my big fur. A dressier moment for a gathering that was mostly family—but one thing about me is I am going to dress up. It was a great outfit to ring in the day Santa’s coming!!

Charty Tip: If dressing up brings you joy, that’s reason enough. Not everything needs to be practical, subtle, or approved. Be extra. Dress for vibes, not the occasion. If it makes you feel good, that’s the only requirement.

Another festive lookbook in the bag. Moral of the story? You don’t need a brand-new wardrobe—or a holiday invite every night—to dress like you’re celebrating something. Sequins on a Tuesday are allowed. See you in 2026 ✨

LOVE YAAAAA,

Charty

P.S. Let the record show: once the parties ended, I spent the rest of the holidays in leggings and sweatshirts at home. Sequins out, elastic waistbands in.