WDW’s 50th Anniversary Tee!

Let’s talk about how this WDW 50th Anniversary Tee came together…

WDW 50th Anniversary T-shirt

When you’re headed to Florida to celebrate WDW’s 50th Anniversary for your 5 year Wedding Anniversary, you need a fun new t-shirt to celebrate! …It’s become part of our tradition after all.

When I began the process of picking out the design, I thought everything would run fairly smooth like usual. However, I’m not going to lie, this t-shirt was a bugger to make! I experienced a couple of different mishaps, but since the shirt is actually finished I can laugh about it now.

First off, when I set out to weed this shirt I didn’t realize how intricate some of the detailing was. I’d say it probably took me 2 hours to weed this thing – Oy. I took a break about half way through because my eyes were going buggy. I decided not to leave it unattended on my desk, however, because I didn’t want JuJu to walk by and get it all hairy. So I grabbed what I thought was a transfer sheet to cover it up. When I came back later I discover that I must not have grabbed transfer paper because it had stuck to the transfer and I had to spend about 30 minutes scratching it off. What a mess!

The next thing that happened was that my Cricut Easy Press tripped a fuse as it was heating up. Down went all the things in my room – the heat press, the tv, my computer, and all of the lights. Thankfully my studio was the only room on that particular breaker and I was able to easily restore it… but I definitely unplugged a few things before turning my easy press back on.

Once those things were taken care of I proceeded to press the shirt. For the most part it turned out pretty well. I did have to take a pair of tweezers and weed out any of the excess paper leftover from my first mishap… but that ended up being super easy – thank goodness!

In the end, I decided that it will be a LONG TIME before I ever attempt to make this shirt again. I had thought about making matchy-matchy ones for Rafe and I but forget about it! I’ll find a different design to work with. I will say, though, that Close To My Heart’s Heat Transfer Vinyl is a DREAM to work with. Weeds easy, transfers smoothly and the overall look is absolutely beautiful. I can’t wait to dream up my next project!



CTMH Black Heat Transfer Vinyl

Provided right is a visual link of the Close To My Heart Black Heat Transfer Vinyl I used. When you click on the link, a new browser window will open up. This makes it easier to shop my Close To My Heart Website for the items you need.
I also used…

  • My Cricut Easy Press – 12″ x 10″ size
  • Weeding Tool
  • T-shirt, any color
  • An incredible .SVG File that I purchased from JennyLynnWestSVG

Have questions about the ingredients listed above? Please be sure to Contact Me so I can help.


Want to see a quick video on the pressing process? Check out my Leggings, Leaves & Lattes video! I even set it up so that the page will open in another browser window so that you don’t lose your place with this project.

Now let’s get creating!

WDW 50th Anniversary Cricut Design by JennyLynnWestSVG
  1. Open up Design Space and click to start a new project.
  2. Next, click on Templates and search for ‘Tee’. Choose ‘Classic T-shirts’ for your template. You will also want to choose the Type and Size of the t-shirt you will be using.
  3. To upload the .SVG file click upload on the left side menu.
  4. Click ‘Upload Image’ and choose the .SVG file you want to use for this project.
  5. Next, choose your uploaded image from the Recent Uploads that are showing at the bottom of your screen and click ‘Add to Canvas’.
  6. Position the cut file where you want it on the t-shirt, adjusting the size as needed.
    NOTE: For this particular file I also grouped all the images together so that they would all remain in-tact.
  7. Click ‘Make it’ and then click ‘Mirror’. This will ensure that the text is readable. Click Continue.
  8. Set your base material to Everyday Iron On, or to the type of heat transfer vinyl you are using. Begin cutting your pieces.
  9. Weed your vinyl pieces and place them on the t-shirt where you want them.
  10. If using CTMH Heat Transfer Vinyl you will want to set your Easy Press to 305 degrees and press for 15 seconds.
    If using a different company’s Vinyl, check out this Cricut Heat Guide before proceeding. Then, use a Heat Press to press the vinyl pieces to the t-shirt as directed.
  11. Peel when the project has cooled slightly. Wash inside out before wearing.

And there you have it. Another beautiful project with the Cricut Easy Press.


I hope you enjoyed today’s project. If you have any questions about this project or my instructions please don’t hesitate to ask. That’s what I’m here for.

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