Our Favorite Holiday Dresses & Skirts

Although Christmas is still 18 days away (but hey, who’s counting?!), we have a few holiday parties to go to before it gets here. And if you’re anything like us, we like to have one or two go-to holiday looks ready for these holiday parties so we aren’t stressing over what to wear and can simply re-wear that holiday look to each party (don’t tell anyone!).2016-DIY-Playbook-Christmas-Card-Casey-Bridget-gift-boxjpg
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Today’s Holiday Staple: Dresses & Skirts

Today, we’re diving into each of our holiday outfits this year (Casey in a dress and Bridget in a skirt) and rounding up some of our favorites in each of those categories. Hopefully these tips and tricks will provide you with a little inspiration to choose your “fancy” holiday outfit. And heck, once you find “the one” that you feel comfortable in, you can wear it on repeat all month long!



I am all about a LBD, especially during the holidays. I probably own 3-4 black sheath dresses that I’ll wear for work and I fancy them up to make them more special for the holidays. 2016-DIY-Playbook-Christmas-Card-wrapped-gifts-Casey-dress

That usually involves adding a pair of fun heels (like these black sandals!), as well as a bit of sparkle. 2016-DIY-Playbook-Christmas-Card-wrapped-gifts-red-box-with-bow

My go-to statement necklace instantly adds some glam to this plain black dress, and you can’t go wrong with some bangles & sparkly bracelets too. Really anything with a hint of glam is bound to take your LBD to the next level.


Since it is a bit chilly now, I’ll often wear an edgy blazer over my dress that I can then ditch once I get indoors. This dress with a hint of texture was a Nordstrom rack find, but I’m always on the lookout for flattering black dresses that can take me from work to night with just a few upgrades to my accessories and makeup!


Don’t get me wrong, I LOVE dresses but the dress I wore in our holiday card isn’t my favorite for the holidays because it shows so much skin (yikes). If you haven’t noticed, I have a VERY fair complexion (read: I’m super pale all the time) so showing that much skin in the dead of winter is not the most flattering look for me. So usually during this time, I opt for a holiday look that is still super fun and somewhat fancy… but also covers up my pale skin!


When I saw these long pleated skirts in stores, I knew this look was calling my name this holiday season. I actually scored this navy skirt last year on clearance from H&M but linked a very similar one, that’s in stores now, from H&M above. I love the subtle pattern on both options but love the plain, patternless skirts too!


The long skirt is comfy and can easily be dressed up when paired with a fancy blouse, or dressed down when paired with a more casual blouse like this one.


The only negative about these skirts is that they tend to be snug around the waist, which is a great way to show off your figure, but not so great when you’re enjoying those big holiday meals. <— aka, there’s not much room to loosen the waist but there is some room to hide the “I’ve-eaten-way-too-much-and-swear-this-isn’t-a-baby-” bump.


Of course I HAD to add a bold statement necklace to the look to make it feel even more glam for the holidays.

If you’re looking to add a pleated skirt to your holiday wardrobe, I would give you the advice to try to find a more form-fitted blouse to pair with it. I tend to shy away from those blouses and usually buy more loose, flowing shirts but those don’t do you any favors when paired with a skirt like this (trust me!!).

holiday_christmas_bridget_skirt_gift_necklace-5But the real question is, do you guys think I can pair tights with this look!? I’ve seen some great inspiration outfits on Pinterest that make tights and a puffy skirt look adorable and I’m hoping that’s the same for this outfit in case it’s crazy cold (… OR I want to hide those pale legs!).

Holiday Dress & Skirt Favorites

Here’s a round-up of some of our favorite dresses and skirts to help you get some inspiration for your fancy holiday outfit. Hopefully, once you invest in a quality dress or skirt, you can wear it all December long… and even into the New Year!

Drape Front Dress // 2. Wool Pencil Skirt  (in all colors!) // 3. Swing Dress (long option)
4. Navy Skirt // 5. Plaid Skirt // 6. Lace Pencil Skirt
7. Classic LBD Dress // 8. A-Line Skirt // 9.Peplum Dress


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.

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