What To Wear to School Classroom Holiday Party

Welcome back to our 12 Days of Holiday Outfits series, a style collab with me, Cyndi from Walking in Grace & Beauty and Kristin from BonBonRose Girls!!

12 Days of Holiday Outfits

It’s been a few days since we’ve posted one of these, so here’s a recap. So far we’ve discussed What to Wear for Thanksgiving, What to Wear Black Friday Shopping, What to Wear to a Company Holiday Party, What to Wear to a Home Holiday Party, What to Wear in Family Photos, What to Wear for a Holiday Date Night, and What to Wear to a Holiday Brunch.

Today we’re talking to the moms out there. Or I suppose this post might be appropriate for teachers too.

With three kids in public school, I always get roped into chaperoning at least one classroom holiday party, and of course I want to look festive! But festive does NOT have to mean this.

What NOT to wear: Christmas Sweater

When I taught school in 1997, that was cute. Today? Not cute . . . unless you’re going to an Ugly Sweater Party, which I personally think is an abomination. Why would I waste an opportunity to dress up in something festive and chic? I do not understand.

We can do better. We are more evolved in 2014. Here’s a casual festive outfit that I put together on Pinterest. Now THIS is PERFECT for wearing into your child’s school for a holiday party. I love the fair isle hat and scarf from Boden. They add such a wintry flair to any simple outfit. Otherwise, this is basically an everyday sweater, jeans and boots combo. Of course, you can go with the expected red and green, but I like the unexpected combination of coral and jade green in this outfit.

Fashion Over 40: Casual Winter Outfit for Moms

Shop this look: Boden Fair Isle Hat // Boden Fair Isle Scarf // Boden Mohair Mix Sweater // DL1961 Florence Skinnies in Topeka Wash // Frye Phillip Harness Tall in Grey // Buxton Leather Bucket Bag at Kohl’s // Stella & Dot Goddess Teardrop Earrings (my go-to earrings right now!!)

Here’s how I would translate this look with what I have in my closet.

I know I said that I like the idea of going with something OTHER than the predictable red or forest green, but you certainly can’t go wrong with that either. This is the sort of thing I typically wear — a cozy red sweater with skinny jeans and my comfy UGG boots. Add some jewelry and a cute handbag, and I’m good to go! (And maybe a bit more makeup next time… lol.)

Fashion Over 40 | Casual Winter Outfit

Shop this look: red cowl neck sweater via Banana Republic // DL1961 Florence Skinnies in Topeka Wash // Grey UGGs (old) // Stella & Dot Snakeskin “The Switch” Tote // silver earrings and bracelets from my Stella & Dot boutique

Or, you could go with grey and black and a pop of red in your shoes or another accessory… such as these red boots. I wore this outfit last Christmas to a play we attended. I felt comfortable yet festive.


Shop this look: grey tunic (similar) // black leggings // Hue Wide Waistband Leggings // red boots c/o JAFA Shoes // Brasilia Crossbody c/o Baggallini (similar) // mixed metal earrings c/o Studio Jewel

Any cute, put-together casual outfit is appropriate for these occasions. I definitely advise leaving the yoga pants at home, but it’s also not necessary to dress to the nines. It’s fun to throw in a little red or green or a fun wintry look as I pictured above with the Fair Isle pieces from Boden. But most of all, bring your camera and enjoy being a part of your child’s holiday celebrations. It’s hectic right now, but I have a feeling that we’ll all look back on these days wistfully.

Now hop on over to see the festive looks that Kristin and Cindy put together!

Join The Conversation

6 Responses

  1. Love these looks – similar to what I wear teaching 1st grade almost every day in December. I recently got a red puffer vest that I’m looking forward to using for some festive outfits. As for the Ugly Sweater Parties, I hosted one a few years ago and thought it was great fun. We had a contest for the ugliest sweater and ugliest gift. You have to think of it like a costume party.

  2. I love those red boots! And a pair of boots with leggings/skinnies and an oversized sweater is one of my favorite winter outfits. Great ideas for the casual holiday party!

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