Disclosure: This post contains affiliate links.

Now that Thanksgiving is over and we are officially moving on to the winter holiday season, I am getting excited about all of the parties, gatherings, good tidings, and cheer to be had over the next several weeks.

My husband and I have a few fun events to attend before the end of the year, including our family Christmas celebration (which we are hosting for the first time). Some of the gatherings will be more casual, while others will require some swanky dressing on our part.

With all of that in mind, I started shopping this week for different outfit options to wear throughout the holiday season. I know, I know, it is still early, but I like to be prepared when it comes to my fashion picks. 

Today on the blog I am sharing with you an adorable and festive pairing that I put together at J.Crew Factory.

I picked up this outfit with the intention of wearing it on Christmas Eve. 

I paired this ensemble with my Sperry Duck Boots {shop them here}.

Typically, I wouldn’t pick such a bright red skirt, but I love this one for the winter holiday season. As soon as I put it on, I knew it was going home with me.

My favorite things about these “sidewalk” skirts from J.Crew are their elastic waistband, their pockets, and their length. This one hits right above my knees, which makes it perfect for the office and for play. I truly cannot stress to you enough how comfortable these skirts are — they’re a staple in my wardrobe. 

Shop this post:

I paired the red skirt with several tops before I landed on one that I really liked —this lightweight navy and white striped turtleneck.

I can’t tell you the last time I wore a turtleneck (I usually can’t stand things around my neck), but I was drawn to this one for some reason. I am certainly glad I stepped outside of my comfort zone and brought it into the fitting room with me. 

Tip: When shopping for new fashion, try on things you typically wouldn’t. Clothes always look different on your body than they do on display, so you might be surprised by how much you like something once you put it on.

To jazz it up just a little more, I added a beautiful plaid scarf that I had been eyeing online for a while. 

It is a gorgeous mix of red, navy, yellow, and hunter green, and I love the contrast of the plaid against the horizontal stripes of the turtleneck. 

I also styled the outfit with my favorite taupe knee-high boots, which I snagged at Marshalls earlier this year for $20. 

I have a few other refined and pretty holiday outfit ideas from J.Crew Factory below.

Enjoy and let me know if you scoop up anything I shared!

Additional holiday season style options
from J.Crew Factory:

Option No. 1

Navy and white turtleneck with a ruffle-front wool mini skirt, paired with the same plaid scarf above. 

Option No. 2

Plaid popover blouse with a ruffle collar. This exact one isn’t available online at the moment, but I linked two similar styles here: Cotton poplin pintuck popover & Glen plaid shirt. This top is styled with my beloved red sidewalk skirt. 

Option No. 3

The same plaid popover blouse with a ruffle collar from above, this time with the ruffle-front mini. 

Option No. 4

One of my favorite flannel shirts — how gorgeous is that green — paired with the red skirt. This outfit is extremely festive for any holiday celebrations you attend this season. 

Happy holidays, y’all!