{seasonal style} "Caps For Sale" Halloween Costume + 17 More DIY Costume Ideas

Last year, I showed you some photos of my boys' "Caps for Sale" Halloween costumes a few days after the holiday, but since it was post-Halloween and no longer timely, I didn't share the tutorial at that time. But I have received quite a few questions about the DIY elements of the costumes, so I thought that this year I would provide the quick how-to well in advance of the holiday.

And today, I've joined with some other fabulous bloggers that have created 17 more fantastic DIY costumes for kids and adults alike. You'll find photos and links to all of these other fun costume ideas at the end of this post!

*This post contains affiliate links.

If you are of the Reading Rainbow generation {like me}, then you're likely to recognize my kiddos Halloween costumes right away! And if not, then you are probably pretty confused. The good news is that son would be happy to explain by reciting the entire book for you, word for word {as he tried to do on each and every porch where we trick or treated last year}!

"Caps for Sale," by Esphyr Slobodkina, was one of my favorite book as a child, and now it has become one of my boys' favorites as well. For the better part of a year, this book was our must read before bed every night! If we tried to skip it... well, we couldn't. Skipping it just wasn't an option!

About a month before Halloween last year, I excited suggested to Beckett {then 2 and a half} that he could be the peddler from "Caps for Sale" for Halloween. I expected a resounding yes, but instead I got a flat NO. After lots of questions about what he did want to be, we finally settled on a different costume idea.

But, in true kid fashion, just two days before Halloween I picked Beckett up from preschool, only to learn that he had told all of his teachers and friends that he was going to be the peddler, and that his little brother, Cooper, was going to be a monkey. When I reminded him of the costumes we had planned, he cried and begged to be the peddler. He was just too cute to say no to, so I spent the next two days making calls and driving around town to find the right colored caps and a monkey costume {there was no way I was going to try to DIY the monkey at the last minute}.

For those not familiar with the story of "Caps for Sale," let me explain...

"Once there was a peddler who sold caps. He carried them on top of his head. First he had his own checked cap, then a bunch of gray caps, brown caps, blue caps, and red caps on the very top. He walked up and down the street calling, 'Caps! Caps for Sale! Fifty cents a cap!'"

"One morning he couldn't sell any caps. ... 'I think I'll go for a walk in the country,' he said. He walked for a long time until he came to a great big tree. 'That's a nice place for a rest,' thought he. So he went to sleep."

"But when he woke up, all the caps were gone, except his own checked cap! He looked to the right. He looked to the left. He looked behind the tree. No caps. Then he looked up, and what do you think he saw?"

Monkeys!

"On every branch sat a monkey. On every monkey was a gray, or a brown, or a blue, or a red cap!"

And so the story continues as the peddler tries to get his caps back from the monkeys. If you have kids and don't know this book - you really should buy it or check it out from the library, because it's a very fun story!

In the book, the monkeys tease the poor peddler, but in our version, the peddler and the monkey are actually best buds!

Caps for Sale Monkey Peddler Halloween Costume

Ok, so now that you're all caught up...let's talk about the costumes. I drove to just about every costume shop in town, I finally found one baby monkey costume in stock that actually looked like a monkey {most others looked much more like bears}.

Next up, I had to find the hats for the peddler. Luckily, Beckett already owned a black and white checked hat and a gray hat {both cabbie style from the boys' department at Target}, and I already owned one blue beret {from a prior French costume party}. But, per the story, we still needed a red and a brown cap for Beckett, and we also needed one more cap for Cooper-monkey.

After trips and phone calls to many costume shops, I finally found one that had a tan beret and two red berets in stock. At 7 pm. The night before Halloween. Talk about cutting it close. {If you are planning ahead, even just by a few days, you can save the hassle and order the colors you need here.}

Fortunately, I have the best husband and the best mom! Scott drove across town to buy the hats after work, and my mom showed up at 10 pm with all the other needed supplies in hand:

Thread - red, blue, beige, gray and black
Needle and scissors
Batting
Elastic
Safety pins {several}
Optional - fake pocket watch and ribbon

The blue beret that I already owned was gathered with elastic, but the red and tan berets had wide openings that were going to make them difficult to stack with the other hats. So the first thing we did was use a simple, temporary, gathering stitch around the base of the red and tan hats. For this, we used a contrasting thread that would be easy to see and clip to remove later - it didn't matter that it didn't match because this stitch would not be visible once the hats were stacked.

After my mom stitched all the way around the base of the hat, we pulled the thread tighter to gather in the base of the hat. Here's the difference between the flat red beret and the one with the gathering stitch.

Once the red and tan hats were gathered, we filled each hat {except for the black and white checked hat, which would go directly on Beckett's head} with a little bit of batting. In the book, the peddler has multiple hats of each color in his stack, but since we were using just one of each, adding the batting gave the hats more volume and ensured that the stack of hats would sit taller on Beckett's head.

Once the hats were filled, we then used a wide running stitch to stitch the hats together, one on top of another, in the order described in the book - first the checked cap, then a gray cap, brown cap, blue cap, and a red cap on the very top. As we stitched the hats together in a stack, we matching the thread to the upper hat each time.

Finally, we stitched a piece of white elastic to the bottom, checked cap. This elastic went under Beckett's chin, making it easier for him to keep the stack of caps on. {They also sell flesh colored elastic that would have been even better, but we were working with what we had.} To attach the second red beret to the head of the monkey, I just used a couple of safety pins.

In the book, the peddler wears checked pants, and black jacket, and a black bow tie of sorts. Since I was pulling this costume together at the last minute, there was no time for checked pants, so we improvised and had Beckett wear his black suit pants. pinstriped suit vest. a white dress shirt, and a black bow tie. For trick or treating, we also added his black tweed peacoat to pull the whole outfit together {and keep him warm, or course}.

My mom happened to have some cute fake pocket watches {purchased at Hobby Lobby}, so tucked one into the top of Beckett's vest pocket flap. We stitched a short piece of silver ribbon around the top of the pocket watch, and then tacked the ribbon down to the vest. This held the watch in place, but was easy to clip and remove after Halloween, returning his suit vest to it's original state.

Here's how it all came together...

Beckett really wanted to carry his book trick or treating with him, but instead I made each of the boys a bag for their candy with the cover of the book on one side, and a picture of their character on the other side!

Caps for Sale DIY Halloween Trick or Treat bags

These bags were a last minute addition {even more last minute than the costumes}. The bags only took me about 5 minutes to make and were completed right before we went trick or treating. I had a couple of small, colorful tote bags left over from a prior project {each is only about 6 inches square}.
I used the copy machine in our home office to copy the front cover of the book directly on to white iron on transfer paper, and then I did the same with two internal pages from the book.

The key here is to make sure your transfer paper is made for use on dark colored fabric - like this Avery Dark T-Shirt Transfer Paper! Once I had the book pages copied on to the transfer paper, I simply cut them out and ironed an image on to each side of the bags. Every brand of transfer paper has slightly different instructions for how long to iron, so be sure to carefully follow the packaging instructions. Nearly a year later, the boys are still carrying their toys and treasures around the house in these cute little bags.

There you have it... a peddler and a mischievous monkey from the classic children's book, "Caps for Sale."

The boys have yet to decide what they want to be for Halloween this year, but I'm hoping we'll be able to make a decision and pull it all together before Halloween-eve this year. I'll be sure to share some photos when the time comes, but in the meantime, here's a look at their costumes from 2013 - Peyton Manning and his football {and mom and dad dressed as referees}. You can find the full tutorial for this football brothers Halloween costume here {including the DIY pads and the DIY football onesie}.