Holiday Pajama Guide for 2019

I am in total disbelief that October has already come and gone. The fall months seem to fly by faster and faster every year. And while I am not one to advocate for skipping over Thanksgiving (I am already dreaming about eating a mountain of mashed potatoes), I also love to get the most bang for my buck! We wear holiday pajamas year round, and I love building the anticipation of the season and letting the boys pick their newest pair. If you want them for the season, now is the time to buy them. In fact, some of the pairs I love have already sold out (you all are shopping early this year!) Below my holiday pajama guide for 2019 is broken down my retailer. Whether you want to something traditional or fun, pricey or affordable, I have you covered!

team santa red white striped pajamas black faux fur trapper hat

Fur Trapper Hats // Pajamas // Fur Lined Boots

Holiday Pajama Guide for 2019

Hanna Andersson

deer fair isle red and white pajama set

Dear Deer Pajamas

matching family pajamas dear deer long john pajamas red and white

Shop Our Family Pajama Set

These pajamas 150% live up to the hype and price tag. The boys got a pair for Christmas last year, and they are thick, incredible quality, and so cute. We actually would pack these to bring to the late last spring when the nights still got super cold, and they have been the first pair the boys whipped out once the temps dropped again this fall. If you question if these are worth the investment..YES. Order a size up, and your kids will easily get two years use out of them!


Old Navy

Old Navy is one of my favorite retailers for so many reasons. A good portion of my wardrobe comes from their online tall shop, and they also have the cutest (and affordable) pajamas. They have entire lines dedicated to dressing the entire family this year. And compared to other family holiday pajamas, at Old Navy you can get your matching PJs in regular, petite, plus, and tall sizes! Plus, so much BUFFALO PLAID. All the heart eyes!


toddler boy christmas pajamas red and white christmas pajamas trapper hat photo ideas for kids red and white team santa raglan top pajama set

This is one place that I might suggest waiting to shop until the Black Friday deals hit. They have been famous for launching a $5 sale on their Christmas pajamas, but when it goes live is never released. Sign up for their e-mails, because once the sale starts, the pajamas sell FAST. I went ahead and paid way more than $5 for the ‘Team Santa’ pajamas below-I wasn’t sure if they would be a part of the sale, and have already sold out so I didn’t want to risk waiting! And, if you are looking for some grown up footie pajamas, look no further than Carter’s, they have you covered!

Gap and Gap Factory

One of my favorite places to buy cute clothes for my boys has always been The Gap, but I swear Gap Factory is a hidden gem that people don’t know about! They have items that are in the main store for SO much less. The red and white bear pajamas are style that is brought back year after year. I threw in a picture of Jackson wearing them as a teeny little thing because I am feeling sentimental 🙂 And they have been marked down as low as $10 on Gap Factory! And do not even get me started on the holiday Snoopy and Woodstock pajamas-SO CUTE!

If you are looking for family pajamas, the main Gap website has tons of adorable options too! Gap Factory has incredible prices, but The Gap has amazing sales and deals too, and so many cute styles!

I hope you liked this roundup! When do you let your kiddos start wearing holiday pajamas? 

If you are already chomping at the bit like I am when it comes to all things Christmas, you can see my Holiday Home Tour from last year here! 

team santa pajamas black fur trapper hat fur toddler bootsteam santa christmas pajamas dear deer pajamas holiday pajama guide


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