Outfits For All Your Holiday Events From Thanksgiving Dinner To Picking A Tree

It’s about to be the most fun time of the year to get ready. You can honestly do so much more around the holidays because you can play with layers and there are acceptable occasions to wear all the glitzy, sparkly items in your closet you’ve been waiting to wear all year.

But at the same time having so many events can be stressful. What’s appropriate? What do I have that will work? A little planning ahead of time and I promise it won’t be so bad. So get out your calendar and get a mental image of what’s in your closet already. Let’s get started!

Thanksgiving Dinner

You may already be listening to Christmas music. (I certainly am.) But you can’t forget about Thanksgiving, which (in case you did forget) is fast-approaching! Stick to autumnal-toned colors for the perfect Turkey Day outfit.

Casual Family Thanksgiving Dinner

Not everyone dresses up for Thanksgiving, but the same idea still works. The brown corduroy pants give it that touch of fall, but the chunky knit keeps it casual so you won’t feel overdressed in front of all your aunts and uncles.

Christmas Shopping

I promise Christmas shopping is more fun if you wear a big teddy bear coat. It’ll keep you warm, and let’s be honest, it’s just so much more fun than a plain old black coat. I mean, come on, that fuzzy texture will have you wanting to give yourself a hug. And hey, it doubles as a security blanket if someone tries to fight you for the last toy or something. (A reminder: it’s always better to just walk away.)

Picking out the Perfect Tree

Take a break from the red with a warm, neutral outfit out in the trees. Let the green of the trees speak for itself! You pair jeans or pants with chic rainboots to be both functional and chic!

Seeing Christmas Lights

You can’t beat a dashing coat for a simple but super chic look for going on a tour of the local lights. Don’t be surprised if the pretty pattern has another woman paying more attention to your coat than the houses. “I have to know where you got it!” It works for school drop off and the grocery store too. You’re welcome.

Holiday Cocktail Party

That holiday cocktail party you have? Don’t shy away from the glitz and the glamour. A sparkly fun dress will do and for a romantic touch add the perfect headband. Statement earrings work just as well!

The Zoom Cocktail Party

Admittedly, things look a little different in 2020. So break out some party pajamas. How glamorous are those feathers? Pretend you’re Audrey Hepburn in Breakfast at Tiffany’s in your comfy glam and get your Zoom on.

Dreaming of a Little Blue Box under the Tree

Speaking of Breakfast at Tiffany’s, I have to say I think Holly Golightly would approve of this holiday take on the color blue. Add your favorite jewelry, and Eartha Kitt will be singing “Santa Baby” before you know it. You’ve been an awful good girl after all!

Seeing the Nutcracker

Whether you’re seeing the Nutcracker or a holiday music concert, embrace a big skirt and tights. You might not be able to get away with an actual tutu, but a skirt that’s almost like tulle will do just fine!

Far from Snow This Year? Embrace the Tropical Feel

If all of this looked like you would have to move so it could get cold enough for you to wear anything close to what I’ve described, this might be the look for you. Simple white neutrals can help you get a beach take on the holiday season. Does Santa Claus come to Newport Beach? (You bet he does!)

Pretend You’re Spending Christmas in the Big Apple

And then there are those of us who like to pretend we’re walking through Central Park and watching the Rockettes at Radio City Music Hall. Black, white, tights, boots, and go just a little (or a lot) over the top. You look like a New Yorker already! And if you’re actually there you can get away with something like this.

Christmas Eve Dinner

You know you're going to spend the next day cuddled up in pajamas, so take advantage of Christmas Eve to dress up! Mix up the red with a gorgeous green skirt or dress. Pair it with a red lip if you want a little pop.

Casual Family Christmas Dinner

Honestly, as much as  I love dressing up, my family keeps Christmas pretty causal. If yours is the same or your new in-laws are this way, grab a funny Christmas sweater. The holidays are all about letting loose and having fun with the people you love. 

Looking Chic on Christmas Morning

A simple white sweater and a silk headband will have you looking chic even at the early hour you know you’ll be up opening presents. Hey, sometimes people have a camera out during that part. A girl’s gotta do what a girl’s gotta do.

Honor Your Matching Pajamas Tradition

Whether it’s just you this Christmas or you’ve got the whole gang, it’s always more fun when you wear Christmas pajamas. Warning, if done every year, you’ll amass quite the collection. I mean, not that it’s a bad thing — I can never have enough!

Seeing That Christmas Day Premiere in the Theater

A coat, scarf, leather boots, and you’re ready for the movie theater. Do it right and the outfit will look like the perfect Hallmark holiday outfit you’ve been trying to recreate for years. 

New Year’s Eve

New Year’s Eve is all about the glitz. So make sure your dress has some sparkle and shine to it. After all, it’s one of the last opportunities you get to wear holiday dresses until next winter.

Skiing

The holiday fun doesn’t have to quite end with New Year’s. After all, the world is about to turn into winter’s playground — if you’re lucky to live somewhere where you get all four seasons. (As a Southern Californian, I’m jealous. So live it up!)

Closing Thoughts

To me, the holidays are the most fun time of the year for fashion. I mean when else do you have so many opportunities to dress up or, at the very least, get out your sparkly sweater? Have fun with it, don’t stress too much, and you’ll be fine. Happy Holidays!