hwtm icons row

Cozy-Chic Holiday Entertaining Tips {+ Free Chalkboard Style Printables}

Quick Jump To » Comments

holiday wine party centerpiece

Well, with Thanksgiving next week, the holiday season is officially upon us… and on that note, I have SO many good things to share with you today!

We’re going to start with some stylish, yet surprisingly simple holiday entertaining ideas, then you’re going to find links to download the chalkboard-style holiday printables that I designed for this post (they’re free!), and then I’m going to tell you about a chance to win a $5,000 Living Room Makeover. I know that last part especially caught your attention, right? ;)

First things first though, let’s talk parties…


Holiday entertaining comes in all shapes and forms, and while the fancy celebrations can be a fun change of pace, there’s so much more to seasonal entertaining than those “all-out” evenings. In fact, the first images that pop in my mind when I hear “holiday entertaining” are not of intricately styled dessert tables or gold glittered everything…

Instead, I see smaller gatherings with close friends & family, in a comfortable, yet festive environment (even if that just means lots of string lights), and with plenty of 2 key things flowing: great conversation and great wine! This kind of gathering is still manageable amidst crazy holiday schedules, and can even come together in the form of an impromptu moment sometimes. That’s why I’m really excited to share this project with you today…

free printable holiday poster

14 Hands Winery, a fantastic brand that you may recognize from some of my Kentucky Derby party related styling for them over the past few years – asked me to come up with some holiday entertaining inspiration to share this season, and specifically requested that it NOT be over the top. Hmmmm… I think they might be on to the fact that we don’t always have a slew of extra hours available to devote to prepping for a get-together. ;)

Of course, I still want anything that I share with you guys to be helpful and creative, because that IS why you’re here in the first place, right?

So, I decided to host a little holiday themed get together with the goal of sticking to a good balance of entertaining style and ease, and of showcasing approachable, yet effective ideas.


I also invited a few friends over and turned this into an actual party, because – A) who was going to help me eat all this food – and B) why not?! And truth be told, everyone was more than happy to have a good excuse for a girls night. ;)

simple and stylish holiday entertaining ideas

I restrained myself from embellishing every square inch of space on the food/drink station (which was set up in my kitchen) – and instead focused on simple, fun things that still made a big impact – like adding little “scarves” to the wine glasses (literally this is just tying a certain type of yarn onto the stem, but it looks cute!) and giving simple appetizers a playful name, like “LOGS in a Blanket”.

logs in a blanket appetizer

Other tips I used for making things festive, yet manageable:

1. Keep food dishes simple, but well presented.

Example: turn a cheese ball into an “apple” with the help of a cinnamon stick & bay leaf.

holiday appetizer - apple cheese ball

2. Feature similar flavors/textures throughout the party to tie everything together.

This makes planning easier too because it narrows your focus. Example: I focused on apples as a key flavor at this party. You can see them reflected in the decor, the food, and the drinks!


That’s Crescent Wrapped Baked Apple Brie pictured above. It’s sooo good and super easy to make! (You’ll see a close-up of it further down the page.)

Another thing that was super tasty? The signature drink… Caramel Apple Sangria! I used this recipe but swapped the suggested moscato for the 14 Hands Hot to Trot White Blend, which I definitely recommend since the drink is still very sweet without using a sweet wine as the base.

caramel apple sangria

3. Use your regular holiday decor as “party decor”.

Example: Pull decorative elements from other rooms/shelves to temporarily deck out the food/drink area at your gathering.

rustic winter holiday decorations

4. Add style with paper details.

This one is always a go-to for me. It’s affordable, fast, and super effective. Example: I put a paper sign into one of my picture frames to turn it into a “themed” tray for the coffee table.


Here are a few more highlights from the evening, starting with that close-up of the insanely tasty apple brie that I promised…

baked apple brie

I also served Spicy Cranberry Salsa for a festive twist + a variety of Food Should Taste Good artisan chips…

simple holiday appetizer ideas

Angry Orchard Hard Cider added some more apple-inspired flair…


casual holiday party


Cheers! I was especially fond of the Caramel Apple Sangria myself, which is not super shocking since caramel is my favorite flavor. ;)


Thanks again to 14 Hands, and I hope you found some tips & ideas here that will prove helpful this holiday season! If you have questions on anything shown here, please feel free to ask me in the comments section below. And now onto everything else…


Click on a link to download the high-resolution PDF file:


14 Hands has partnered with Angry Orchard and Food Should Taste Good to offer up a $5000 Living Makeover (in the form of a Crate & Barrel gift card) to one lucky person. Talk about HAPPY Holidays for the winner! ;)  To enter, simply fill out the sweepstakes entry form here.


  1. @honestywedding November 18, 2014 at 3:51 pm

    Cozy-Chic Holiday Entertaining Tips {+ 14 Hands Wine & Free Chalkboard Style Printables} #catering #wedding http://t.co/Da7jZhhF0z

  2. Liz November 18, 2014 at 6:36 pm

    I love the printables. I can’t wait to try that cute wine wreath and those great recipes.

  3. @HWTM_Jenn November 19, 2014 at 11:36 am

    Tips for hosting a casual-chic holiday party, featuring clever recipes + @14handswine + free printables! :) http://t.co/Zh7K2BKzpS

  4. Crystal Hall Barnard November 19, 2014 at 6:38 pm

    THANK YOU :) this is a great find ….

  5. Amy November 23, 2014 at 4:33 pm

    Love the party printables. Check out my birthday party printables: https://www.etsy.com/shop/MilestoneMemory

  6. Jacqui Odell November 23, 2014 at 4:49 pm

    These are great tips! Everything looks geat

  7. Nikki November 30, 2014 at 1:45 pm

    Love the caramel apple sangria idea, definitely using that soon. Simple decor is always the way to go in my opinion.


  8. Lidia September 9, 2015 at 11:14 am

    Thank you ! just love those printables <3

    Greetings from Marbella Spain

  9. David Head October 2, 2015 at 7:39 am

    Looks tasty. Wine is very sweet and lovely to have with evening meals, will have to try and make it.

Comments are closed.

Browse Party Ideas: