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DIY Jack Skellington Shirt & Pumpkin

Make a DIY Jack Skellington shirt and pumpkin using HTV and adhesive vinyl with this free cut file!

This is a sponsored post on behalf of Expressions Vinyl and Getaway Today. As always, all ideas and opinions are my own.

This post contains affiliate links.

Make a DIY Jack Skellington shirt or decorated pumpkin using HTV and adhesive vinyl!
My family traveled to Disneyland a couple of years ago during fall break.

All of the Halloween decorations were up, and my boys, then 3 and 6, were going to go trick or treating in the park.

We saw so many fun characters that night we trick-or-treated that I was convinced we would have never seen them all during regular park hours.

One character we missed, because his line was sooooo long was Jack Skellington.

It was just as well since my boys hadn’t seen The Nightmare Before Christmas yet and didn’t know who he was.

However, the next day we saw Jack Skellington with only a small line shortly after entering the park.

My boys had spotted him and, though not knowing his character, really wanted to meet him so we got in line.

And I’ve been kind of obsessed with him ever since!

As you can see, my boys were not the least bit afraid of him.

In fact, they were pretty fascinated!

And Jack did great with the boys.

He explained to them that he had taken over the Haunted Mansion ride, which we hadn’t been on yet.

He wanted to be sure he could hear us all scream as we rode it.

Running into Jack Skellington prior to riding the Haunted Mansion turned out to be a super happy accident.

The boys were so enthralled by him that they weren’t the least bit scared on the ride and looked for “their friend, Jack”.

When we came home from the trip we let the boys watch The Nightmare Before Christmas for the first time, and they really enjoyed it.

Meeting Jack Skellington in person made it much less scary!

Make a DIY Jack Skellington shirt or decorated pumpkin using HTV and adhesive vinyl!
DIY Jack Skellington Shirt

Re-watching the movie with my boys made me remember how much I loved Jack’s character.

Now I’m little obsessed with using him at Halloween!

Last year I made my boys The Nightmare Before Christmas Halloween trick or treat bags.

This year, I used the SVG pattern from the bags to make myself a fun Halloween shirt and a matching pumpkin for my decor!

You can download the FREE pattern for Jack Skellington’s face here.

I cut the main characteristics of Jack’s face out on black glitter heat transfer vinyl (eyebrows, eyes, nose, mouth, and tie).

Note: Remember, when cutting HTV flip the image horizontally prior to cutting.

The only piece that needed weeding was the tie.

Place the cut HTV on a white t-shirt, cover with an piece of cloth or ironing mesh, and iron the vinyl on.

Peel up the plastic cover on each piece of vinyl while it is still warm.

Make a DIY Jack Skellington shirt or decorated pumpkin using HTV and adhesive vinyl!
DIY Jack Skellington Pumpkin

I found a small, round pumpkin at Michael’s that was the perfect shape for Jack’s head.

It was cream colored so I simply gave it a quick coat of bright white acrylic paint. I also painted the stem black.

Resize the image of Jack face to fit your pumpkin and cut out the eyebrows, eyes, nose and mouth on black glitter vinyl.

Use transfer tape to pull up the cut image, started with the eyebrows, eyes, and nose.

Position where you want the vinyl on the pumpkin then use your thumb the rub the vinyl on.

This will help keep a smooth application over the ridges of the pumpkin.

Repeat the process with the mouth, applying a small portion at a time.

Make a DIY Jack Skellington shirt or decorated pumpkin using HTV and adhesive vinyl!
Isn’t that just too fun?

I love that the glitter vinyl gives Jack a little sparkle in his eyes.

And the classic black and white is perfect for Halloween.

Make a DIY Jack Skellington shirt or decorated pumpkin using HTV and adhesive vinyl!
I am going to wear out this Jack Skellington shirt this October!

And I for sure can’t wait to wear it to Disneyland when we go back next year during fall break.

Maybe I can get my picture taken with Jack Skellington!

If you’re a Nightmare Before Christmas fan, too, try making these DIY Jack Skellington shirt and pumpkin yourself!


26 MUST SEE Disney Crafts all using vinyl!
Be sure and visit the other 25 Disney craft ideas using vinyl that my fellow bloggers have created!
1. Lion King shirts by Play Party Plan
2. Jack Skellington Ears by A Pumpkin and a princess
3. Nemo pumpkin from C.R.A.F.T.
4. Disney coloring shirt by Artsy Fartsy Mama
5. Belle framed art by Crafting in the Rain
6. Miracles free cut file By Dawn Nicole Designs
7. Autograph shirt by the Pinning Mama
8.Disney countdown by Frenchi Wraps
9. Girl dress up by Over the Big Moon
10. Spirit animal shirt by Smashed peas and Carrots
11. Customized Minnie Ears by Inspiration Made Simple
12.Winnie the Pooh quote from Where the Smile Have been!
13. Modest ariel from Kiki & Company
14. Jack Skellington coin purse by Tried and True
15. Minnie Mouse purse by A girl and a glue gun
16. Disney ornaments by Happiness is Homemade
17. Girl Boss shirt by Sweet Rose Studio
18.No Sew Minnie tutu by Sugar Bee Crafts
19. Haunted Mansion door design by Simple simon and Co.
20. Minnie Mouse bow shirt by Girl loves Glam
21. Mary Poppins design by the Crafted Sparrow
22. Cinderella hand lettered shirt by Pitter and Glink
23. Jack Skellington shirt and pumpkin by the The Scrap Shoppe
24. Beauty and Beast book sign by Flamingo Toes
25. Hat hair shirt by Polka Dot chair
26. Vintage Disneyland by Persia Lou



>> See where I party! <<

Don’t miss these other Disney-themed cut files!

Hocus Pocus Cut Files mickey mouse autograph book jack skellington cut file nightmare before christmas trick or treat bags star wars dark side propaganda shirt

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Barbara E Schatz

Tuesday 12th of October 2021

I am trying to print out the Jack Skellington design for a shirt like you made. I am using my cricutjoy and design space. I canot get it to work the image goes grey and no matter how big or little i make each section it still says incompatible can you please help me out?

Michele McDonald

Monday 18th of October 2021

Unfortunately I do not use Design Space so I am not sure how to fix that problem, but I did add a PNG version of the Jack Skellington image in hopes that it will work better for you.

Julie Briones

Tuesday 8th of October 2019

And Disney lover would LOVE this shirt! So cute! We missed you at Tuesday Turn About last week! Hope to see you this week!

Lorrie Hansen

Friday 22nd of September 2017

Do your files come in SVG???

Michele McDonald

Saturday 23rd of September 2017

Unfortunately not. They are Silhouette Studio files. There is no simple way to convert them without downloading extra software and jumping through hoops.


Tuesday 12th of September 2017

What a fun shirt! My oldest daughter just got back from two weeks in Disney with her best friend. Thanks for linking up at #HomeMattersParty


Sunday 10th of September 2017

What a fun memory for your family. Lo-ove the t-shirt and I know my son will, too. Thanks for sharing at the This Is How We Roll Link Party.

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