What to Wear this Holiday Season

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Plaid Shirt  |  Jacquard Skirt |  Shoes  | Similar Necklace

What to wear…what to wear?  This time of year there are extra events, parties, work functions and celebrations {not to mention the piles of laundry you don’t have time to get to!} so clothing choices can be just one more stressful thing. Today I have rounded up some basic, but stylish, holiday outfits to make getting dressed in more than Christmas pj’s effortless, and many of these items are on sale. Worth the mention, these are all outfits that Christy and I own and are wearing in real life 🙂 not dressing room photos.

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Wrap Sweater ($22 on sale!)  |  Dressy Dark Jeans  |  Leopard Pumps   |  Silk Cami  |  Pearl Statement Necklace

This first outfit will take you almost anywhere, and at this time of year it is nice to know you can walk that line between being dressy without being overdressed, especially if you aren’t sure of the dress code. Blush pink is a hot color too, so you will be right in style with this sweater–at just $22.  I mixed a silk camisole (also perfect under a casual cardigan) with the wrap sweater to dress it up then added this pearl statement necklace along with classic leopard pumps–you can’t go wrong with these gorgeous shoes! Also-another similar option, maybe a little dressier, for the sweater is HERE.


Similar Sweater  |  Plaid Pants  |  Flats

Christy put together this classic holiday outfit {above}, I love these plaid pants. This is another can’t go wrong/when you don’t know what to wear look.  These pants also look sharp when worn with a crisp white shirt, a nice one is here. Classic shoes and pearls will take you just about anywhere during the holidays.

NOTE: Right now LOFT is having a 50% off sale, which is pretty much the best deal they offer. We weren’t planning on publishing this post until tomorrow but jumped ahead because so much of what we wear is from LOFT so this is the best time to shop! 


Bell Sleeve Sweater   |  Pink Velvet Pants  |  Leopard Flats  |  Similar Necklace  |  Similar Booties

Christy put together this pretty outfit above that also has many LOFT items, like these beautiful pink velvet jeans (seriously, who does not need pink velvet jeans?!? I definitely do!),  and this soft bell sleeve sweater. I like it with both the leopard flats and the boots, this is perfect for a day of running around and finishing up all that holiday shopping.


Plaid Vest (40% off)  |   Similar Sweater  and HERE|   Plaid Shirt  |  Hunter Boots  |  Boot Socks  | Necklace  | Similar Bag

How cute is this plaid vest– and it is on sale! It is just so perfect for the holidays. This outfit can go anywhere this month–shopping, parties, school concerts– it is comfortable and cozy.  Christy and I both have this vest, it will definitely get you in the holiday spirit!


Similar Fur Vest HERE and HERE  |  Tartan Shirt  |  White Cords  |  Gray Suede Boots (sale!) |

Pearl Necklace 

This outfit {above} will be my Christmas Eve outfit. I have gotten so much use out of this plaid shirt already this year, and you can find a similar pattern here for just $23 today.  I love it with the fur vest {mine came from Stitch Fix, but I’ll share with all of you that I have this pretty gray one on my Christmas wish list this year, yay for it going on 40% off sale!}. Pairing this outfit with white cords dresses it up a bit, and the gray over the knee boots are on major sale so scoop up a pair (or ask Santa for some) they are truly a great item to have in your wardrobe.


Vest  |  Striped Top  |  Jeans  |  Riding Boots  |  Necklace ($12 shipped!)

Here’s another basic but still cute for running around town and doing all that Christmas shopping outfit. This outfit also looks great with black leggings, though I am showing it here with my favorite jeans (this version is on sale).  I have gotten so much wear out of this military vest this fall and winter. I also tried it with the pearl necklace {yes here it is again!} and loved that to0, see how that looks below.


Pearl Necklace

I hope these outfit ideas are helpful. Before I sign off and since I can’t pass up a good sale 🙂 especially at this time of year when I am always looking for cozy sweaters. I really wanted to order this sweater, I have been wishing for it all Fall but unfortunately it is already sold out in my size 🙁 scoop one up if you wear a medium or large, same with this popular one). I ordered this cozy sweater and this tunic sweater, I am sure my husband will appreciate less shopping to do for me 🙂

Speaking of holiday gift shopping, if you still need ideas you can see all our gift guides HERE. 

Have a lovely day!


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Our posts contain affiliate links.  If you make a purchase after clicking on these links, we will earn a small commission, which helps to keep our content free.  You don’t pay a cent more than you would otherwise, since that would be tacky! Please see our full disclosure policy here.

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