When we were getting ready to go to Disneyland, I knew that I would need to pack hats for all the boys to wear. We were going to be outside in the sun for more than 11 hours until the sun went down, for 3 days in a row. But it’s September; No one is carrying kid baseball hats this time of year because they have already clearanced all “summer” items and moved in the winter gloves and beanies. Sooo, what was I going to do???

I wanted us to have/make matching hats, just as I made matching shirts and backpacks. I decided to let the kids all pick their favorite Disney character to paint on their hat. I wanted to buy white hats because they would match any shirt and they would be the coolest option. But I still had this dilemma of not begin able to find any hats. I looked to order hats online, but that would mean spending way more than I wanted to {$9-$20 per hat}. The kids and I wandered around different super stores {Walmart, Target, etc.} hoping to get lucky and find kid hats that were white and on clearance. We weren’t lucky. I passed by the men’s area in Walmart and spotted that they have year-round baseball hats that are solid colors, that cost less than $4 a piece. Perfect. I decided to buy us each a man’s hat and alter the boys if I needed to. So this tutorial is not only on how to paint Disney characters on a baseball cap but also how to alter a man’s hat to fit a child.



Step 1: Prep

Begin by keeping the cardboard insert in the hat so the paint doesn’t seep through to the other side. Now I placed a ruler on the front of the hat to see about how big I wanted the characters.

Note: The sizes I chose ranged between 2.4″ and 3.2″Disney Hats

For my template, I made everyone’s favorite character paired with the character’s name. Then I cut the template out of vinyl to use as a stencil. Download this zip file for all the SVG and PDF files for Winnie the Pooh, Mickey, Buzz, Baloo and Minnie. Download Icon

Step 2: Stencil Placement

Take stencil or vinyl and stick to hat. Place vinyl, with it’s backing still on, where you want it on the hat and tape down. Flip up and remove backing. Spray vinyl with a tacky spray. I use Easy Tack by Krylon. Flip vinyl back down on the hat and press firmly. Remove the transfer tape slowly making sure all the vinyl stuck well to the hat. Note: This can be a little tricky because the hat is a rounded surface, instead of a flat surface like a shirt.

{For a step-by-step picture tutorial on how to stick the stencil correctly check out this post.}Disney Hats

Now place the template on the hat. If using freezer paper, iron it into place. If using vinyl, stick it on using this method with tacky spray. I also have a video here that shows how I do it using another shirt I made.

Step 3: Painting

Take sponge brush with fabric paint or acrylic paint {mix the fabric medium with your acrylic paint to make the paint flexible to help prevent cracking when washed} and dab paint within stencil/vinyl.

Step 4: Alter Hats, Optional

The men’s hats were way too big for my kids. So here is how I did some quick altering to help the hats fit securely on their heads. I began by cutting off the velcro tab on one side. I then pinned it directly to the hat and sewed it on securely. Note: I even did this step, of relocating the velcro, on mine.Disney Hats

Disney HatsI then had each child put on their hat to see how much the hat was gaping at the back, top of the key-hole area. I then pinned a silly little tuck into the back so that the hat fit snug. I stitched it down with a straight stitch, going over it a few times to make sure it would stay. Done. That was easy.Disney Hats

Disney HatsStep 5: Finishing

Once the paint is completely dry {I wait 12-24 hours, just to make sure} remove the vinyl stencil and cardboard from inside the hat. Then place a piece of scrap fabric over the painted areas and heat set the paint with a hot iron. This step is a little tricky on a hat. Just don’t misshape the hat while heat setting the paint. I ended up holding the hat in my hand and gently rolling the iron around the shape of the hat.Disney Hats

Ta-da! You are done. Now you and your little ones are ready for all the sun exposure you can and will get at Disneyland. Don’t forget {I did} to get a picture of your little one wearing their hat with their favorite character. The character will be so excited to see that they are your little one’s favorite.Disney Hats