Matching Family Pajamas for Holiday

Happy Thursday, friends! It’s an exciting day over here… Mr. College is headed home for Winter Break today, and I can’t wait to have my people all together again!

He still has finals and projects for the next week, but just having him at the dinner table makes me excited! I may have gotten used to him being away, but setting the table for three still gives me a lump in my throat sometimes!

Plus, now that he’s home, we can begin all our family Christmas traditions like looking at lights, going to the symphony, watching Elf, etc. No matter how old they get, both my kids still look forward to the traditions we started when they were little.

Well, all except one tradition… matching pajamas, ha! That one takes a little more finagling on my part, and has evolved a bit over the years. But they always end up having fun with it!

I also learned that mix-and-matching classic prints is much easier to get everyone on board with, rather than the same Christmas print for everyone. This year I found the softest, coziest, and cutest prints for us all at Gap!

*Photos by the darling and talented Audrie Dollins. This post is created in collaboration with Gap and ShopStyle Collective, but all product selections, styling, and wishful thinking are my own. Thank you for supporting Hi Sugarplum sponsors!*

Flannel Pajama Set (on sale!) | Sweater Socks

Flannel Pajama Set (on sale!) | Sweater Socks

Gap has so many fun prints to choose from, but I’m always drawn to the classic tartan plaid. These are super soft cotton blend with a brushed flannel feel, and the cutest plaid for holiday and all winter long. Plus, thanks to Gap’s Must Have Gifts Sale, they’re all on sale, PLUS an extra 30% off with code YOURS!

They have sizes and options for every member of the family… even the pups!

Waffle Henley Tee | Flannel Pajama Set | Cozy Socks // all on sale!

I also like to break up the sets with every day tops like this henley… helps me get away with wearing them all day, ha! I grabbed an extra pair of these cozy socks for Little Miss’s stocking, and these for the guys.

Waffle Henley Tee | Flannel Pajama Set | Cozy Socks // all on sale!

Flannel Pajama Set (on sale + extra 30% off with code YOURS)

Flannel Pajama Set (on sale!)

Waffle Henley Tee | Flannel Pajama Set | Cozy Socks // all on sale!

I love mix-and-matching styles to create a cohesive look for the whole family! Here are some fun options in the classic tartan plaid… all of which work great well past the holidays! And yep, all on sale plus an extra 30% off with code YOURS!

mom: Flannel Pajama SetClog Slippers
dad: Henley TeeMicrofleece Joggers
dog: Pajama Shirt
sister: Cami PJ Set | Sherpa Hoodie | Sleep Mask
brother: Henley Tee | Robe | Flannel PJ Pants

And these are so cute in a traditional red. Now all I need are some cooperative teenagers, ha!

mom: V-Neck Jumpsuit | Sherpa Boots
dad: Waffle Knit Tee | PJ Pants (Similar HERE) | Sherpa Pullover
dog: Sherpa Onesie
sister: Sherpa Sleep Hoodie | Santa Socks
brother: Plaid PJ Set (Similar HERE & HERE) | Clog Slippers | Logo Hoodie


Flannel Pajama Set (on sale!)


I’ve ordered sets for everyone in the family, and hoping to catch them all in a festive mood. I may get my Christmas wish of matching pajamas after all! Ha!

Think about how cute Christmas morning pics will be in these!! Now’s the time to grab them during Gap’s Must Have Gifts Sale. And don’t forget code YOURS gets you an extra 30% off! Not to mention, so many great gift ideas, especially for the littles. I mean, this cute find makes my ovaries twitch!

Does your family or kids wear matching pjs? Which color way are you drawn to most… the blues and greens, or classic red?

Leave a Comment


  1. Mary wrote:

    The pj’s are so cute. I kinda like the blue/green this year! I got a pair for both me and the hubs.

    Posted 12.9.21 Reply
    • Cassie wrote:

      YES! I was loving the green and blue as a change of pace too!! xo, C

      Posted 12.10.21 Reply
  2. Christine R Bates wrote:

    Where did you get the stocking hat? So cute!

    Posted 12.12.21 Reply
    • Cassie wrote:

      It’s an oldie from TopShop. I have a thing for Pom Pom beanies!

      Posted 12.16.21 Reply