The BIG Holiday Outfit Post: Outfits To Take You Through the Season

Today is the first of our three BIG holiday posts this month…we’re here to help with your holiday outfit! Check back next week for ALL the holiday gifts guides, and we’ll have stocking stuffers after Thanksgiving.

You’ve been RSVPing to all the events, and now it’s time to decide what to wear. You’re in luck, because we’ve been busy planning holiday outfits for wherever you’re going! From Thanksgiving dinner and Christmas caroling to cocktail parties and New Year’s Eve, we’ve got you covered with something to wear.

We hope you’ll use our guide as inspiration to create your own holiday look. Start by shopping your closet, and then shop our links to add in the pieces you need. And don’t forget the accessories to add some extra sparkle for the season!


5 Staple Items You’ll Want in your Closet this Season

If you’re looking to stretch your wardrobe dollar this holiday season we think these are the items you’ll want to have in your closet. All of these items can be worn many ways, can be dressed up or down, work for many occasions, and will serve you well beyond the holiday season.

Coated Denim and Vegan Leather: This is the chameleon of your closet because they can look super fancy with one blouse, but then look super trendy with another! If you haven’t gotten the fan favorite vegan leather pants from Gap (Megan’s faves) be sure to check them out.

A Versatile Slip Skirt: They’re everywhere! Try the trend with this under $30 skirt from Amazon, available in tons of colors and patterns. Again, the slip skirt can be dressed up or down depending on shoes and accessories. A great travel piece.

Something Sparkly: A clutch, shoes, or earrings are easy ways to add sparkle! We have lots of accessory options at the end of the post.

Black Pants You Love: You know we have a few recommendations! Try the Wit & Wisdom (Christa’s pick) or the Liverpool (Megan’s pick).

Dark/Flared Denim: A dark denim can be dressy, especially with a wider leg. Try this new pair from WHBM (shown below).


Megan’s Slip Skirt for the Holiday Season

I’m officially declaring it slip skirt season. This navy slip skirt is so easy to style and it’s very comfortable — perfect for all of your holiday outfits. The hidden elastic waist makes it “buffet friendly”. Easily dressed up with a cashmere tee shirt, gold sandals and gold accessories, you can also style it more casually for lunch with friends or a day of hitting the museums. Per usual I’m going with the column of color — all navy (or any color) creates a slimming silhouette.

No matter how you are celebrating the holidays this year, add a slip skirt to your closet and you won’t be sorry. There are endless ways to style it. This skirt is the perfect, most versatile item to take on a trip. You could easily make this black tie(ish) or pop on your sneakers, a graphic tee and a jean jacket for a day of shopping.


Christa’s Casual Holiday Look

I have several casual parties this holiday season, and these shoes will be coming with me to all of them! Heck, they’re perfect to wear anywhere in the month of December. They’re about $60 on Amazon and so cute! They’re a comfortable 2″ block heel. This brand on Amazon has 15 different styles in holiday plaid, everything from flats to block heel to kitten heels. Order them soon so you have them for the holidays — some of them don’t ship via Prime.

Sweater note: This sweater is too heavy for me so I’m not keeping it. I’ll be looking to complete my look with either a lighter weight red sweater or red blouse.


Friendsgiving Dinner

thanksgiving dinner outfit idea


Thanksgiving Dinner

*This dress is currently on major sale!


Black Friday Shopping


Gift Wrapping


Favorite Things Party


Holiday Dinner with the Girls


Holiday Dinner with Friends


Christmas Morning


New Year’s Eve (Early Bird) Dinner in the City


A “Mario Party” New Year’s Eve


Add Some Sparkle with Accessories


Looking for some holiday decorating inspiration? We’ve linked some of our favorite decor this season. Click here for details.

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