It’s Rocco’s first Halloween where he will go out trick-or-treating. He doesn’t understand what Halloween is, but we are excited to bring him to our friends’ house to go out for the first time with their two kids who are a bit older than Rocco.

When we first started thinking about what Rocco should be this year, Jade and I conceded that for at least one Halloween, Rocco had to be Rocky the flying squirrel. Not only because of their shared name, but the sheer cuteness factor of our son in a little DIY aviator hat and large squirrel tale seemed too good to pass up.

A Rocky the flying squirrel costume isn’t really something you can buy, so I decided to dive into sewing. I haven’t sewn anything since I made my own ladybug costume in college. The twelve-plus year absence from sewing seemed daunting, but Jade eased my anxiety by finding an original owner’s manual online for my 1970’s hand-me-down sewing machine. To get my creativity flowing, he also showed me this example of a homemade aviator hat another blogger made.

Based on her version and this arming cap template I found, I plunged into creating a Rocky version of an aviator hat. I visited a local fabric store, and I was totally overwhelmed with the selection. I managed to wrangle a preoccupied employee to direct me to the type of fabric I should use. She pointed me toward stiffer cottons and just my luck, I found some remnant in a perfect blue color and some soft fuzzy gray material for the tail.

Creating the DIY aviator hat went quite well. Using the pattern I’d found online, I simply traced the pattern on the blue material, cut it out, and pinned the pieces together. The first version was too big on Rocco, so I took in the seams another ½ inch. It was a simple enough fix and fit him as well as I could expect for a homemade hat. I also lined the hat in some of the furry gray material for comfort (the blue material was a very stiff cotton) and to give the hat a more finished look.

To make the goggles, I bought some black pleather and some clear vinyl material. I created a pattern by drawing a free hand pattern based on this aviator goggles image. I initially tried sewing the goggles onto the hat, but found they puckered too much, so I removed some of the stitching and only sewed down the bottom and sides of the goggles, along with the strap in the back.

The first tail I made resembled more of a cat’s tail — thin and curly — so I scratched that version, and bought some shaggy fur from Michael’s. I made another tail pattern that was larger and less curvy than the first. The second tail turned out quite large—probably large enough for an adult squirrel costume.

When I showed Rocco his large tail, he actually got scared and started semi-crying. Despite his protests, I attached it to a footless gray onesie I picked up at Ross. I hand stitched the tail to the back of the onesie.

Since Rocco’s initial reaction to his squirrel tail was fear, we thought we should do a test-run with him in it. He was not having it. Jade and I both had to wrestle with him just to get it on. After I snapped the leg buttons and the costume was in place, Rocco tentatively walked around the living room. Jade and my enthusiasm, smiles and laughing encouraged Rocco to check himself out in the mirror.

The tail was so large it was throwing his balance off. He was leaning back and walking with his legs wide spread apart to keep himself from tipping over. Jade and I laughed for a long time, but that only egged Rocco on. Once he stumbled in front of the mirror and spotted the tail behind him, he quickly loved his costume. After several minutes of proudly walking around the living room, I moved toward him to take it off. He screamed and protested. He absolutely didn’t want to take it off. I can’t tell you how happy I was that he loved his costume.

Despite the failed first attempt at a fuzzy tail, and a really obnoxiously large second tail (which is hilarious), we love his little Rocky costume. No, it’s definitely not perfect, but it was a lot of fun for me to make and even more fun to see how much Rocco enjoys wearing it. Plus, this is his first Halloween when he will go trick-or-treating, so it feels even more special that I made his first real Halloween costume.

Have you made your kid’s costume before? What are they dressing up as tonight? Happy Halloween everyone!