These ugly Christmas sweater lollipop covers made the perfect little additions to the treats my son passed out at his school’s holiday party!

My son, Rowan, is in Pre-K and he really wanted to pass out Christmas gifts to all of his friends at school this year. Momma here, however, doesn’t have a wallet the size of Santa’s bag, so we went for a less expensive route….lollipop treats!

Just any ol’ sweet treat wouldn’t do though. Nope. Not happening.

I love the ugly Christmas sweater phenomenon that has taken over, and when I found the cutest reindeer head lollipops, a lightbulb went off: Combine the two into a festive and adorably ugly personalized little gift that Rowan could pass out at his class’ Christmas party! Bingo.

Personalized Ugly Christmas Sweater Lollipop Covers

Would pre-schoolers get the whole ugly Christmas sweater thing? Probably not. I’m sure their only concern was getting those lollipops unwrapped and into their mouths ASAP. I mean, I don’t blame them.

However, the parents will probably pick up on the reference, and I sure had fun creating these suckers (Ha! Suckers….lollipops….get it?). ;)

Either way, these reindeer are dressed to impress and my son was so excited to hand them out. Mom FTW!

Time-Lapse Video

Here’s a quick run-down of this fun holiday project!

Supplies

Here’s what I used for these sweet treats:

I wanted these covers to be dual-sided with a cute holiday design on the front and a personalized ‘Merry Christmas’ message from Rowan on the back.

The lollipops just slip right down through the neck hole and then into loops at the bottom of the front and back hemlines, with a couple Glue Dots securing the sleeves together.

And wham-o! The reindeer are looking mighty jolly indeed.

The Ugly Christmas Sweater Lollipop Cover Designs

I designed these ugly Christmas sweater lollipop covers in Silhouette Studio since I’d be cutting them out with my beloved Silhouette Cameo as a print-and-cut project. It’s pretty much my go-to for these kinds of things.

Silhouette‘s print-and-cut function is the bee’s knees and I use it all. the. time., especially when my son needs to pass out treats at school. It makes creating unique personalized goodies SO easy.

Here are some Valentine’s Day creations that Rowan has passed out to his classmates over the past couple years (and you can snag the free printables/cut files too!):

Cutting Out the Ugly Christmas Sweater Lollipop Covers

After my designs were finalized and cut lines ready, I printed them out three at a time on some sheets of cardstock.

All that was left was loading each printed sheet into my Silhouette Cameo and cutting them out….then of course giving them their reindeer heads.

A few moments later, the covers were cut and looking adorably ugly!

After removing them from the cutting mat, I simply folded each sweater in half along the perforated cut lines at the neck and folded in the loops at the bottom, then inserted the reindeer lollipops.

The Completed Ugly Christmas Sweater Lollipop Covers!

And here’s how they turned out! I think they are just the cutest little things in the history of ever. My son let out the biggest chuckle as soon as he saw them. My husband just closed his eyes and sighed while shaking his head. I know that means he loves them, too.

Rowan had a blast handing these out at his party, and by the looks of his friends’ faces, they sure enjoyed eating them. It was a party full of holly jolliness, indeed….as well as some craziness too since it was a bunch of four- and five-year-olds ramped up on sugar and Santa and gifts.

Oh what fun! :)