I just had to make my cool dude a cool pumpkin t-shirt!  What’s cooler than adding shades?  This Jack-O-Lantern with Sunglasses SVG makes for the perfect DIY Halloween Shirt.  Even better my guy has missing teeth to match the shirts jack-o-lantern smile!

Orange Shirt with Jack-O-Lantern Face wearing Sunglasses
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DIY Iron-on shirts are probably the #1 thing I use my Cricut for.  With 3 kids and so many “special” days at school, my Cricut lets me whip up “special” shirts in minutes along with my EasyPress 2.

If you aren’t familiar with a Cricut, you can read all about the Explore Air and the Maker as well as everything you need to know about Iron-on as well!  I even have a post dedicated to every tip and trick I know to correctly apply Iron on so that it sticks wash after wash!

Supplies for Halloween Jack-o-Lantern Shirt:

How to Cut Iron On using Cricut

First, you will upload the SVG file into Cricut Design Space and then size it to your t-shirt.

Next, Click Make It in the upper right corner of Cricut Design Space.

Don’t forget to Mirror your image

Click Continue after you Mirror your Image and connect your machine.

Select your material (which is Iron-on) and Load your mat.

Cricut Maker Machine cutting black iron on for Jack-o-lantern Shirt

Press the Cricut C to start cutting!  When it’s finished weed your design using a weeding hook.

You may find detailed directions with photos here. 

How to Apply Iron-On to T-Shirt

I am going to use the medium EasyPress 2 size which is the 9×9 inch size with the 12×12 inch mat.  This is the perfect size for a child’s shirt.  If you are making an adult sized shirt the 12 x 10 will be your go-to EasyPress 2 size because you can get the entire design in one press!

9x9 IeasyPress 2 with 12x12 EasyPress Mat

I checked the Recommended Easy Press Settings and set my EasyPress to 315F for 30 seconds.  I preheated my area for 5 seconds, applied my design (carrier sheet UP) and then pressed with my EasyPress 2.

Pressing an Orange T-Shirt with an EasyPress to make Jack-o-Lantern shirt with sunglasses

Everyday Iron on is warm peel.  You can find explanations of warm vs. cool peel here.  I removed the clear carrier sheet when it was cool to touch but still warm.

Now put it on your favorite pumpkin!

Boy sporting Orange Jack-o-lantern Shirt with sunglasses on

Here are a few more Halloween T-shirts and SVG Files:

Here are some of my favorite Pumpkin Projects & Recipes:


Jack-O-Lantern Face wearing sunglasses

This flash freebie is only available at no cost until November 5th, 2018 and it will then move to my shop.

This file is no longer a flash freebie!  You may grab it in my shop!  Be sure to sign up for my emails so you never miss another Flash Freebie!


Create a fun DIY Halloween Shirt using iron on with this Sunglasses Jack-O-Lantern Face SVG File! Bonus if your model is also sporting a toothless jack-o-lantern smile!