How to Make Wheres Waldo Costumes

When planning for this years family Halloween costume, the costume difficulty level and comfort were top of mind. T-shirts, beanies and glasses made Where’s Waldo Halloween costumes an easy choice. I also loved that my pregnant belly could be her on little Wenda too. This pregnant Where’s Waldo costume did involve a tiny bit of sewing for the hats, but other than that it’s just hunting down the right clothes.

Here’s what you need to make Where’s Waldo costumes

For the hats–

Red felt
White felt
Sewing machine
OR hot glue gun
This tutorial on how to sew the hats
OR skip the sewing, and order these 😉

For the outfits–

Red and white striped t-shirts
Kid sized red and white striped t-shirt
Black rimmed glasses (A great deal on Amazon!)
Blue jeans

For the prego belly–

Red and white felt scraps
White card stock
Black marker
Hot glue gun
Safety pin
Tape

How to Make Where’s Waldo Costumes

Let’s talk about sewing the hats for a second, don’t let the whole sewing thing freak you out. And if you don’t have a sewing machine- hot glue works great! I used this tutorial as a guide to make the hats, but I didn’t even sew the bottom of the hats under. After all, it’s just a Halloween costume, who cares! And the hat size thing is kind of tricky, in the tutorial she gives you a free printable pattern for a 6 month baby, but you’ll have to guess to make the hats bigger.

Step 1- Hat sizing

I recommend making the hats slightly too big since you can always make things a little smaller if necessary. Here are my rough measurements for Waldo beanies for the whole family:

Toddler: 10 inches at the base
Woman: 11 inches at the base
Man: 12 inches at the base

The hats are trickiest part of this costume. If you wanted to make things easier, here’s a great deal on a Waldo Beanie! As you can see, 18 month old Maxwell is not a huge fan of his hat anyway. He did love the glasses and kept them on the entire time. I was shocked!

Step 2- Waldo T-shirts

Next, you’ll need t-shirts! One of the reasons I like Waldo costumes so much is because the “costume” can be used again and again. Max wears his red and white striped t-shirt all the time. Here are the best deals on red and white striped t-shirts:

Kid Waldo t-shirt (This is great deal on the whole set!)
Adult Waldo t-shirt (Comes in size small to 3X Large!)

Step 3- Add Wenda to your pregnant belly

Finally, if you are pregnant, add a baby Waldo or Wenda to the belly. I made a flat red and white beanie with felt and hot glue and used a safety pin to secure it to my t-shirt. The glasses are drawn on a piece of white card stock with a black marker. I cut them out and taped them to my shirt. Fancy, huh?!

And me and my 20 week (baby girl!) belly…

And here we are as an almost family of 4 Waldo’s!

Does your whole fam dress up for Halloween? Just the kids? If you’re looking for more DIY costumes ideas , don’t miss:

Here’s what you need to make Where’s Waldo costumes