DIY Pennywise IT Halloween Costumes

Why buy a Halloween Costume when you can DIY an EPIC Pennywise the clown IT costume from almost all thrift store materials and half the price! These handmade costumes combine the original Pennywise, the new updated Pennywise, and of course Georgie for a trio of creepiness that you are not going to want to miss!

DIY Pennywise the Clown Halloween costumes with the original version of pennywise, the new movie version, and Georgie from the movie IT, all holding red balloons.

When I asked my Twins what they wanted to be for Halloween this year, I did not expect to hear “Pennywise” at all! Where did my cute little superhero Twins go?! I guess those years are long gone!

This was the first year (of many) that I decided to go creating crazy and handmake our Pennywise Halloween Costumes from start to finish. I am writing this blog post 3 years late and we have since made DIY Beetlejuice, and this year I am in the process of DIY’ing Edward Scissorhands as well!

DIY Pennywise the Clown Halloween costumes with the original version of pennywise, the new movie version. 2 different handmade costumes with 2 kids wearing them.

When the boys told me they wanted to be Pennywise, my first thought was “How are we ALL going to dress up together?” and then IMMEDIATELY I got the most awesomest idea ever……One of the boys could be the Original 1990 version of Pennywise IT Clown, one could be the new 2017 version, and I could of course be Georgie!

After lots of research, saved Google images, and Pinterest scrolling, off to the thrift stores I went!

Let me show you how I pulled this all together. This post of course will not be a step-by-step tutorial because the items that I used you most likely will not be able to find at your local thrift stores. But use this as inspiration and for ideas of how YOU can make your own DIY Pennywise Costumes for Halloween!

This post may contain affiliate links for your convenience (which means if you make a purchase after clicking a link I will earn a small commission but it won’t cost you a cent more!)

How to Shop for DIY Pennywise IT Halloween Costumes

The best way to find what you need is to save a bunch of Google images to your phone so that you have them as reference photos to take with you thrifting.

Now don’t go saving photos of other peoples DIY Pennywise costumes, save photos from the actual movies so that your inspiration is coming straight form the source and you can get as close to the real deal as possible. Here was my main inspiration… ( I looked at and saved LOTS of other photos too)

A side by side picture of Pennywise from the original movie on the right side with the yellow clown outfit, and the new Pennywise from the remake on the left side with the grey clown suit and fiery red hair.

When you are at the thrift store, keep an open mind! Remember that things can be cut, sewn, dyed, torn, pieced together and altered to make it what you need! I’m not gonna lie, for these DIY Pennywise Costumes, I ABSOLUTELY lucked out on what I found.

Yes, most of this is old lady clothes LOL. But hey, it worked!

A pile of clothes from the thrift store laying on the ground.

My oldest Twin, Justice, dressed up as the OG 1990 Pennywise. We found yellow HUGE old fat lady pants that were just perfect. They were huge! So huge that both Justice and I could fit into them!

Amanda and Justice together inside a huge pair of yellow pants, playing around having fun.

But remember what I said, you can cut and alter them, so I grabbed them anyways and I knew I would make them work.

Maddox, who was the new 2017 version of Pennywise the clown, was a little harder to accomplish. All I found was a large white collared pirate looking shirt and we somehow turned that into his whole costume.

Maddox in an oversized white collared shirt with black ties.

How to make your own DIY Pennywise Halloween Costumes from Thrift Store Materials

Pennywise the Clown – 1990 Original version

To make these pants wearable by a tiny 8 year old, I cut out a huge chunk in the shape of a V out of the back of the pants, and then used Velcro tape and safety pins to close the gap.

A big chunk of the yellow pants cut out to make them smaller.

I didn’t need the pants to fit like pants, I needed them to fit like overalls, so the length wasn’t as much of a problem.

The Pants sewed back together without the bug chunk that was cut out.

This is how they fit once I was done with them. I did end up gluing/pinning straps over the top of his shoulders so that they didn’t end up falling down on him. They pulled up kind of like those rubber pants that fishermen wear.

Justice standing up with his hands over his face wearing the oversized yellow pants pulled up to his chest.

I got 3 big orange pom poms on Amazon and glued those down the front of the DIY Pennywise Clown pants.

The yellow pants on the ground with 3 big orange pom poms glued up the front.

For the Pennywise jacket and vest, I took the large blue and purple dress that I found and cut it right off at the center and it made the perfect jacket! I saved the bottom fabric of the dress to make the clown collar next.

A watercolor blue purple and green womens dress with the top jacket looking part cut off.

To make the clown collar I cut out a semi-circle piece, and then pleated and folded and glued it together at the top to get the ruffled look.

A piece of the purple, blue, and green fabric from the bottom of the dress that was cut off and ruffling it together to make a clown collar.

I found this lingerie LOL- which had the perfect ruffled lacey part- for the top and bottom layers of the collar.

A white lacey piece of lingerie with a ruffled edge that was used as part of the clown collar.

I just cut off that bottom ruffled part, and made one larger peice for the bottom layer, and one smaller piece for the top layer. I attached the collar around Justice neck by adding velcro to the ends and velcroing it in the back, layer by layer. Here is the completed collar!

The ruffled lacey fabric along with the blue. purple and green dress fabric layered on the floor together to make a clown collar.

The last piece of this is the floraly multi-colored vest that the OG Pennywise wears. For this, I just took the tank top I found and cut it into a vest and layered it on top of the jacket.

I did end up buying a wig on Amazon, but it was huge on him. Definitely not the best part of the costume but it was better then nothing. I used white liquid latex to cover the “skin” color and make it white to match his face.

Here is the completed look!

The completed original DIY pennywise the clown costume laid out on the floor with yellow pants, blue and purple top, red wig, and white gloves.

And here is Justice in full costume side by side with my inspiration!

Justice side by side comparison in his original DIY pennywise the clown Halloween costume, next to a picture of pennywise from the original movie.

Pennywise the Clown – New 2017 Version

The first problem with the huge white pirate shirt was that it was not the right color. It was stark white when I bought it, and I needed to make it a grey color. dyed the entire thing with RIT fabric dye in Pearl Grey and ended up with the perfect shade of grey! If you are going to dye fabric, I HIGHLY recommended dyeing a small part first to ensure you are going to get the color you are looking for.

I dyed a pair of old little girls white leggings as well for the Pennywise bottoms.

The white oversized collared shirt cut in half to make it smaller and not as long.

I cut the shirt in half at the waist so that I had a top and bottom to work with. Truly, this was bit of a struggle, but it ended up working out after a lot of playing around!

I used some of the extra fabric from the bottom part to make the Poofs Pennywise has on his arms. I don’t have as many photos of the new Pennywise process, because I was so focused on getting it to look halfway decent LOL.

The sleeves of the white collared shirt ruffled up and stuffed to make them puffy.

I then took some Maroon chunky yarn, and twisted some white string around it to make the arm and waist belt details, and then glued them to the shirt.

Found some maroon Pom Poms on Amazon and glued 3 of those down the front of the DIY Pennywise shirt. I did 2 on top of the belt then glued the belt on and another pom pom below it.

The white new pennywise shirt laying on the ground with large maroon pom poms glued to the front center and lace trim glued to the end of each sleeve.

I used the large piece of fabric from the bottom portion of the shirt to make a sort of stuffed skirt slash shorts type of bottom. I actually stuffed the inside of the “skort” with paper towels to make if puffy like the new Pennywise real costume looked!

The lacey skirt I found at the thrift store made the perfect collar for the new Pennywise costume. I was able to cut a piece of the lace off and use it as detail for the bottom of each sleeve as well.

The completed new version of the handmade DIY Pennywise the clown halloween costume with the grey pants, and the white lace collar.

The new 2017 Pennywise the Clown wig was not quite as simple as the original Pennywise wig that I bought. This one I had to doctor up quite a bit to make it look like the real deal. So much so that I dedicated an entire blog post to just how I made this New Pennywise IT Wig.

It started with this Bald Old Man wig…..

And ended as this amazing fiery red Pennywise the clown wig!

A side by side comparison of the DIY wig that was made with the bald old man wig and the actual wig used int he movie IT.

You can read all about exactly how I made the wig in this blog post HERE.

I finished the DIY New Pennywise costume off by making some boot covers with fabric and a Pom Pom and he was done.

And here is Maddox in full costume side by side with my inspiration!

Maddox side by side comparison in his new updated DIY pennywise the clown Halloween costume, next to a picture of pennywise from the new movie.

Although Maddox costume was a bit of a hot mess, it worked! It definitely could not be worn a second year as it was quite literally taped and glued together, but it did make it through two nights, both the El Cajon Haunt Fest, as well as Trick or Treating!

Maddox sitting on the curb staring off into the distance with the new Pennywise DIY Halloween costume on.

The completed DIY Pennywise the Clown Halloween Costumes – Both the Old and the New Pennywise

How did I do!?

A photo grid showing the handmade costumes on the floor all completed, on the boys on Halloween night. and on the original characters in the movie.

We didn’t enter a contest this year, but we totally should have! People were literally stopping us on the streets and asking to take our picture! Here we are together!

How creepy do these 2 look!?

This was just the start of many DIY Halloween Costumes! Make sure to check out our DIY Beetlejuice costumes, and this year I am in the process of making Edward Scissorhands! *Both blogs coming soon so when you click they MAY or may not be ready- sorry*

Are you going to Handmake your Pennywise the Clown Halloween Costumes this year? Shoot…are you gonna make your Halloween costumes at all?! If you do, I’d love to see it! Pop on over to our free Craftspiration Facebook group, and join in on the fun by posting a pic of your Tiered Trays, DIY’s and crafts. I just love to see all your creative and crafty creations!

If you’ve got a million projects on your crafting ‘to-do’ list like I do, than you need my FREE Craft Project Planner so you can plan to make *all the things*! When you sign up for the craft planner, I’ll also send you lot’s of fun, easy, and budget friendly ideas for you to fill it up with!