Our Favorite Holiday Party Outfits

Is it just us, or does it feel like every evening there’s something on the calendar? Don’t get us wrong, we love spending time with family and friends celebrating the holidays…but dang, things have been absolute craziness lately! Work parties, family get-togethers, holiday happy hours…there is a lot going on right now!Holiday party outfits for the season

If your schedule is the same, we want to help you pick out some new holiday party outfits. We don’t often buy brand new outfits every year for all of those get-togethers. Instead, we add a few key pieces to our wardrobes that we can mix and match. And right now there are some amazing pieces that work perfectly for the holiday season! Stock up on a few of these items and you’ll be set for the rest of the year…

Holiday Party Outfits – The EssentialsBridget's holiday outfit with skirt and top

First, let’s start with the clothing. It’s soooo cold here in Chicago, so we often wear pants and a fun top when heading to Christmas parties (or fun pants and a simple top!). Sometimes we’ll wear a skirt or dress if we want to really take things to the next level, but for the most part, we’re all about staying warm while looking trendy!

Velvet Leggings

Velvet screams holiday and we are both obsessed with these velvet leggings. Pair them with boots and a red top and you’re ready to go!

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Plum Ponte Pants

Ponte pants are the best because they’re comfortable like leggings, but dressy enough for work! We swear by any of the ponte pants from Anne Taylor but are especially in love with these plum-colored ones.

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Lace Pants

How fun are these?! You could pair these gorgeous lace pants with a simple black turtleneck and some heels and call it a day! So elegant, yet fun.

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Green Wrap Dress

Want everyone to be green with envy? Wear this stunning dress! It has stellar reviews and the wrap style is incredibly flattering. Wear with pumps, fun earrings, and a clutch and you’re ready for a night of fun!

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Anthropologie Blouse

This textured blouse with a high neckline is sexy, yet understated. Pair it with sleek ponte pants and a red lip and you’re all set!

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Red Bow Blouse

Neither of us owns much red, but when it comes to the holidays we like to don the color here and there! Love this gorgeous red top with a flattering neckline. Would look great tucked into slim pants or a skirt!

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Sidewalk Skirt

This skirt is so versatile and comes in a few colors that would all work well beyond the holidays. But our favorite part is that it’s stretchy around the waist, so you can indulge in those extra holiday treats!

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Classic Blazer

A go-to blazer is a must for the holidays because it can instantly dress up jeans or pair well with a dress, skirt, or festive pants. We love the cut on this one and you can’t go wrong with classic black.

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Lace Top

This blouse would be perfect for just about any holiday function! With jeans for a girls’ night out, with a skirt for a more formal outing, or even paired with a cute pair of pants and a blazer. So many options!

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Versatile Sweater

Last but not least, we love this puff sleeve sweater… and again, how versatile it can be around the holidays! This could be the cozy yet super cute addition to your favorite ponte pants, velvet leggings, or even tucked into a skirt.

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Holiday Party Outfits – AccessoriesA leopard clutch for a holiday outfit

But you certainly don’t have to buy a bunch of new clothing to be prepped for all of those holiday parties. Instead, pick up a few new accessories and add them to your everyday ensemble. We especially love to add a red lip, necklace, heels, and a clutch to a work outfit and it’s instantly ready for the holidays!

Statement Necklace

We both own statement necklaces from J.Crew and get so much use out of them! Wear over the collar of a button up or jazz up any plain black outfit. A little bling can make anything feel festive!

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Glitzy Drop Earrings

Just like the necklace, earrings can instantly make any outfit look dressy! These gold and black ones would work well any time of the year, but we especially love the statement they make during the holidays.

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Black Opaque Tights

If we’re brave enough to wear a skirt or dress, we’ll sometimes opt for tights underneath. Love these super opaque ones, especially worn with a cute heel!

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Leopard Clutch

A leopard clutch goes with any outfit. Casey has one and swears by it! This one from Sole Society is a great price and can be used all year long.

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Everlane Heels

We’ve heard AMAZING things about these heels from Everlane (just go read some of the 4,000 reviews!). Black suede or black leather would dress up any ol’ outfit for a holiday party!

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Red Lipstick

This MAC lipstick in the color “Ruby Woo” has a cult following because it somehow looks amazing on every skin tone. Sometimes when we want to look pulled together (but we’re faaaar from it!), we’ll swipe on a deep lip and walk out the door with our heads held high!

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Do you have any new holiday party outfits? Do share where you’ve been shopping lately! Oh, and if you want more fashion inspiration be sure to check out our gift guide.


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m married to Finn & mom to Rory and Ellis. Together we’re creating our dream home in Chicago, one DIY project at a time.