Happy Little Hooligans,  The Crafty Crap

Halloween Costume Themes

If my family is known for anything it is for our Halloween costumes. And maybe that our house always reeks of stinky bulldog, or that we have a ton of pilots, or that the kids are… crazy…

But we are definitely known for our family Halloween costume themes.

I wouldn’t even say Halloween is anyone’s favorite holiday, but it has kinda become a thing with my family. Way back when our dogs were our only children, we started dressing them up for Halloween… okay we dressed them up all the time but especially for Halloween.

The first time we did it they were a cop and a robber.

The next year they were Batman and the Joker.

Poster paint, folks. Non-toxic (very important) and washes out of fur so much easier than an oily face paint!

My family all came that year and we kinda sorta dressed up and just hung out in the driveway, and tried to eat all the candy we could before the throngs of children got there to claim it. We all refer to that Halloween as, “the year Jackie was a man.” It totally freaked my dad out and the rest of us just couldn’t stop looking at her and laughing. More than usual anyway.

Somewhere in there, there was a year I had to work. I went as Flo from Progressive. It wasn’t until the end of the day that I finally figured out how to work a Bump It, and one of the parents asked what my name was again, then saw my “name tag” and said “Oh, Flo. I’m sorry.” Still, I loved this costume.

After that, the dogs were Tinkerbell and Peter Pan, complete with tights. While I am still trying to get over the fact that we didn’t win the pet costume contest at our local pet store for the second year in a row (this was only like 10 years ago but seriously, how?!), this was the year it really started.

That year I had invited my family to come over again because Dustin was making chili. You have to offer food to these people to get them to do anything. I had suggested to my mom that since Rugby and Ginger were Peter Pan and Tinkerbell, then we could all be pirates and lost boys. I had pictured one of us with a hook and an eye patch, another with a tattered shirt and crazy hair. Nothing major. Unless you count the cardboard pirate ship I stayed up all night painting. Remember Hudson’s Wild Thing boat? The pirate ship was the first boat I’d asked Dustin to build.

I thought I was really going all out as Wendy with my blue nightgown, but you guys, when my family got to my house, Captain Hook himself got out of the car. My mom handmade everyone’s costumes (they all wanted to be pirates) and in case anyone ever wondered, she is where I get my I-don’t-do-anything-halfway genes.

Jack Sparrow wanted to join in on the fun too.

And here’s an obligatory Captain Morgan picture.

From then on, we have chosen a theme almost every year. The only criteria are that the theme has to have the ability to include everyone and that we shouldn’t have to explain what we are. At first, it was centered around the dogs’ costumes, but they got too old to tolerate it just as kids started entering the picture. Not gonna lie, it is getting harder and harder to find time to make them all from scratch so there have been a lot of store-bought costumes that we simply enhance.

The boys agreed to do The Wizard of Oz as long as they got to pick the next year.

As usual, I was still making my own costume when it got dark on Halloween. Cheap bald caps don’t work when you have dark hair. Nobody knew what I was. But I was a munchkin, okay?!

Also, has anyone ever seen the episode of Parenthood where Mark really wants to be in the family Christmas picture and there’s all kinds of drama because he wasn’t officially part of the family yet? Well, this has been the case with my brother’s girlfriends and my Halloween pictures. But I love, love, loved this wedding dress I found at the Salvation Army and dyed pink. Sigh…

The very next day, Dustin bought a lightsaber from a collector on eBay because letting the boys pick meant we had to do Star Wars the next year.

I was a liiiitle bit pregnant that year. Like, 36 weeks.

I thought I was huge but I think that’s how I looked at about 20 weeks the next go around.

I’m still not sure if this was old man Obi-Wan or Jesus with a lightsaber.

I have no idea how my sister-in-law pulled off this R2D2 so last minute!

And just because I loved this shirt:

The next year we obviously had another person to dress up. Minions sounded fun. And it was!

At this point we really wanted to do something Harper would like, but that the rest of us would have fun doing too. Cinderella was perfect! So perfect in fact, that I convinced my husband the day before Halloween, to go to a public place, in broad daylight, to take pictures.

I mean, look at them!

And the dancing!

And when her shoe fell off (this really happened), Prince Charming put it back on. And it fit!

Just thinking about the slideshow at her wedding makes me wanna cry!

And then there’s this:

And I think this was the year we started to notice a pattern with my dad. His favorite costumes are the ones where he has long hair…

And then there’s my brother sister…

And my mom was too cute handing out her “Cheeeez-Its.”

Aaaand another girlfriend.

The next year we had just moved into a new house and there was little time for planning. We decided that since it was a new house and the new neighbors knew nothing of our Halloween obsession, we could be lazy and recycle an old theme. We went with Peter Pan. Fitting, since this was the theme that started it all and we were starting over again in a new neighborhood. Except I thought by recycling the theme we could recycle some old costumes as well. As it turns out, Captain Hook was the only costume still around. Thank goodness for Amazon and Etsy!

Oh that attitude…

Ever seen a pregnant Smee?

This was also Harper’s first year in preschool. Could she have worn her Tinkerbell costume in the storybook parade? Sure. Did she? No. For one, it didn’t seem all that comfortable for wearing all day. The real reason though, was that if she were to ruin her Tinkerbell costume before Halloween night, the whole theme would be ruined. So instead, she was one of 101 Dalmations. Easiest DIY costume ever.

And probably the cutest too!

The year after that Harper was old enough to have a little more say. She wanted to be Ariel, from The Little Mermaid. Her all-time favorite. Seeing as how she already had this costume, I just needed to get a nude colored leotard and she was done! The rest of the costumes weren’t all that bad either. Please note: My dad, with hair.

Oh my goodness, these two…

As it turns out, I was pregnant that year and by next Halloween, we had a Hulk-sized baby on our hands. No really. I had a giant baby. I thought a baby hulk would be funny, and a superhero theme was born. With so many characters to choose from and so many people that wanted in on the action, it turned into a bunch of people at the last minute. Here’s just a few:

Here’s a girlfriend that’s a keeper.

And again, my dad with the hair.

Harper’s Supergirl costume was handmade by my mom so the quality was superb (as opposed to my single-use only costumes) and it was actually comfortable, so she probably could have worn it to school for her storybook parade. But I’d already set the expectations of getting 2 costumes and she and I had just read Pippi Longstocking. I had always wanted a Pippi Longstocking costume but for some reason never did it. So in order to live vicariously through my child, I convinced her to be Pippi. She remembered exactly how Pippi dressed and there would be no deviations.

Can anyone else lift their horse on their porch?!

And here’s a Mike Wazowski just because.

This year Dustin was scheduled to work, as was just about everybody else in my family, so we didn’t really plan for much except I reeeeally wanted to make Hudson an Ewok. Harper had been asking all year to be a witch so we figured, why not? No theme this year. But then at the last minute, Dustin got the time off. Hudson was already going to be an Ewok and we had an awesome Darth Vader costume that had yet to be recycled at the new house, so I bought myself a Leia costume and we were set. Then Harper got upset about not being in theme with us, so yet again, she had 2 Halloween costumes.

Those boots were my pride and joy until she tromped through enough water to make the points fall off. In her defense, it had rained like crazy and she’s only 5. But man, I loved those witch boots!

I’ll have to do a tutorial on how I made them, but for now, I’m going to bed.

Happy Halloween everyone!

Check out my Halloween Pinterest board for more ideas and send me any group costume ideas you find!


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  • Fashion Styles

    Have you ever thought about publishing an e-book or guest authoring on other sites? I have a blog centered on the same subjects you discuss and would love to have you share some stories/information. I know my readers would appreciate your work. If you’re even remotely interested, feel free to send me an e mail.

    • Jessica

      That’s so nice of you to ask! I love to write, but I think for the time being I’m pretty content to keep it all here on my little blog. I’ll keep that in mind though! 😉

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