Learn how to customize your matching family Christmas pajamas to give them a special homemade and personalized touch! It’s super easy to DIY with your Sihouette / vinyl cutter!

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Hey y’all! Happy December! Here’s a question for ya… are you a matching family Christmas pajamas type of family? Or NOT matching family Christmas pajamas?
I personally can go either way. Some years we match (-ish), and some years we are all doing our own thang. And some years I’ve even skipped on Christmas pajamas all together! (*gasp!* I know! A true Christmas crime. 😅)
When I do go for the Christmas pajamas, I like for there to be something personal about them.
Some years I have made our Christmas pajamas from scratch. As in… bought the fabric, pretended to draft up a pattern, and sewed our cute little pjs all on my lonesome. These definitely have the most sentimental value to me. BUT… I’m not a super gifted seamstress, so not only does this usually become rather stressful, but the final result is not too terribly comfy, cozy. 😝🤷🏼♀️
So… many/most years I just end up purchasing pajamas. But (when I can) I still like for there to be something special about them that relays the fact that I was thinking about each child.
This year, I decided to go “matchy matchy” with our pajamas, but still customize them a bit with the help of my Sihloutte vinyl cutter and some iron-on vinyl. And I LOVE how they turned out. 😍

How To Customize Your Christmas Pajamas
Even though we’re going with matching family Christmas pajamas this year, I still wanted each person to feel unique. So I thought it would be fun to add a holiday word to each of our shirts using some iron-on vinyl.
Choosing Christmas Words
I brainstormed Christmas words that revolve around happiness (cuz we could all use a bit more HAPPY this year 😉), and came up with my favorite six options that coordinated with each person’s personality: Merry, Joy, Jolly, Bright, Cheer, and Jingle. And then I added a hashtag at the beginning of each. Just because.

Other good Christmas word options could include: Peace, Noel, Holly, Glad Tidings, O Come, Star, Angel, Wiseman (or WiseGuy… if you’re being punny😝), and so on. Lots of fun options here!
Once you have your words picked out, you’ll need to format them and get them cut out from the vinyl.
Fonts and Sizing
I have a Silhouette SD vinyl cutter (seriously old school at this point, but still working great). So I used the Silhouette software to format the words in the size and font that I wanted.

I used one of my favorite tall and skinny fonts (‘Jasper’) in font size 195 to get words that are just barely taller than 2″. That was a good middle ground size for all the family shirts. And using that size meant I could fit all the words on one sheet of vinyl.
I try to use my vinyl space as efficiently as possible. No space wasted. It would feel unloved. …It’s almost like a disease y’all. 😂
Iron-On Vinyl
There are TONS of fun iron-on vinyl options to choose from these days. Glittery. Metallic. Iridescent. You name it!
For this project I picked a ‘Sport Flex’ vinyl. Sport Flex has been my favorite iron-on vinyl lately. It’s not stiff, and bends well with the shirt fabric. You know… almost like it’s flexible. Oh, wait… haha. 🤣

So anyway, you can choose whatever iron-on type of vinyl you want. But if you like doing iron-on shirt projects and haven’t tried the sport flex before, you owe it to yourself to give it a go.
Cutting the Vinyl
So you load your vinyl onto your cutting mat and into the vinyl cutter, but WAIT! Don’t cut it yet!

It’s important to remember that when you’re doing iron-on projects (particularly if words are involved), that you need to MIRROR your project before you cut it.
Mirror = flip it backwards so that it initially reads in reverse. You MUST do this because you will have to flip your image again when you actually iron it on… and if you haven’t ‘mirrored’ it prior to cutting, you will now have words that read backwards.
Yes. I have done that. Multiple times. 🤦🏼♀️
Granted, vinyl softwares have gotten really smart these days and many will now prompt you with a question about whether or not you need to mirror the image. But in case yours does not, *make sure* you mirror your words prior to cutting (or have the software mirror it for you).
And then you just let the vinyl cutter do it’s magic. 😉
Ironing the Vinyl onto your Shirt
The final step is to iron your cute little vinyl words onto your cute little Christmas jammies shirts.

A couple tips to keep in mind…
- Double check where the words will fall when the shirt is actually *on* you (i.e. how high or low above the chest line you want it to be)
- It can be tricky to get words straight, so just do your best… keeping in mind that what looks straight on the ironing board may not look straight when the shirt is actually on you due to the way shirts can sit on your shoulders.
- Do not apply the iron directly to the vinyl! After you’ve placed your vinyl where you want it on the shirt, you must place a thin kitchen towel (or something similar) on top of the vinyl to protect it from direct contact with the iron.
- Only use medium… *maybe* medium-high heat on your iron. (Your vinyl will likely have specific directions with it.) But too much heat can cause the vinyl to pucker.
- Be sure all areas of your vinyl get thoroughly ironed, then allow it to cool a bit before removing the backing.
And voila! Your super duper cute, semi-homemade matching family Christmas pajamas are ready to go! Just look how much fun it is! 😁

We’re not weird at all. I promise. 🤣
Where to Find Matching Christmas Pajama Pants
If you’re interested in some help finding cute jammies for your family, I can tell you what worked for us.
For our Christmas pajama pants, I love the red and black buffalo print (which, thankfully, is easy to find right now). I ordered matching pajama pants for each of us (actually, I found my youngest boys pants at Walmart… but the rest of ours I ordered from Amazon).
The microfleece fabric is soft and cozy, which is perfect for these cold winter nights (I totally recommend microfleece). And the fit and comfort is awesome. They make snuggling up next to a fire in the fireplace so darn fun. ☺️
On a side note… I was quite impressed with these pajama pants in the fact that they are so long! Hubby is quite tall (6’5″) but not super large around the waist. So we usually have a hard time finding pants that fit him in length without looking huge and bunchy around his waist. But these pajama pants are really long! So they fit him great! Incidentally… I’m quite short, so they swamp me. But I’m used to that. So I will either just hem up the bottom a bit, or enjoy my extra long jammies. 🤣
Matching Christmas Pajama Shirts
For our pajama shirts, I was originally just going to get a cotton t-shirt. (Least expensive option.) But those aren’t very comfy for sleeping in. So I ended up going with a tri-blend fabric shirt (50poly/25cotton/25rayon). They’re more expensive, but worth it if you’ll actually be sleeping in them.
I purchased our shirts at Hobby Lobby because I needed them right away. But if I’d had a bit more time, I would have ordered them… only because Hobby Lobby didn’t have all the sizes I needed. So both myself and my littlest guy ended up with shirts that are a size too big. 😜 But it is what it is.
The quality of the shirts is great though, and they’re super soft and cozy. But if you plan ahead, you can order them to make sure you get the sizes you need. 😉
I picked a dark heather gray to accent the red and black buffalo pants (as opposed to a black shirt, which would have been a little too precise of color coordinating for my taste) and I love the way they look together. Especially once I added the white customized wording.
But have fun with it! Go all crazy colors. Go super traditional. Go with whatever will make your Christmas magical! And then enjoy it all year long. 😉❤️
Merry Christmas, y’all!!
Shop This Post
- Sport Flex Iron-on Vinyl
- Silhouette (Cameo 4) Vinyl Cutter
- Microfleece Pajama Pants
- Tri-blend Soft Shirts
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