Custom T-Shirts
by Dave

Girl wearing her handmade t-shirt
Spend the afternoon exploring your creative side and making something completely unique. One of the best things about this date idea is that whatever pattern you create, be it an image of a famous person, you and your date’s handprints, or just a block of text that has special meaning, you are making a shirt that no one else in the world will have. Only you. Give it a try, you'll find out that it feels pretty good. This is also a great way to get closer to your date by helping each other with ideas, making suggestions, and working as a team to make the best designs possible. Plus, when you're apart you can put on the shirt and feel close to them again. Sappy, but true.

Custom t-shirts are much easier to create than most people think, but before starting you need to figure out what kind of shirt you want. If you want to transfer a complex image onto a shirt, it will probably be best to make a stencil. On the other hand, if you both just want to have a little fun messing around, you can just use brushes, spray paint, or a sharpie. Think about what you want to accomplish before starting out, it will make the rest much easier. Take a look at the videos in the Links section to see ideas on stencils or doing something simple like hand prints.

First off you’ll need to find some blank t-shirts, maybe 2 or 3 each. They don’t have to be white and you can go with short-sleeved, long-sleeved, v-necks, or whatever. Local stores like Target and Walmart carry blank shirts, or you can probably find better deals online. Try to stick with 100% cotton, it usually produces the best results.

As far as the paint is concerned, there is specially-designed fabric paint like Speedball ($6), regular old spray paint, or even a sharpie. The one downside of standard spray paint is that it’s a little more likely to fade and you will definitely need to hand wash the shirts when they’re dry to reduce fading.

Brushes depend on your design choices. Remember that a thick brush can be used with stencils (even small rollers too) instead of spray paint. You will also need a large piece of cardboard to place inside the shirt so that paint on the front doesn’t leak through and color the back, plus newspaper, exacto blades (for stencil-makers), an old towel or rags, masking tape, and maybe even chalk.

First, check whether the shirts you bought need to be washed before painting. Sometimes they will have chemicals on them that prevent the paint from properly attaching to the material. The easiest way to find out is to put a few drops of water on the shirts; if it beads up, wash them, if it soaks in, you’re good to go. When washing, make sure you don’t use any fabric softener. Also, if the shirts are wrinkled, a quick ironing will make them easier to paint evenly.

At this point you should print or draw your designs on a piece of paper and hold them up against the shirts to get the sizing right. Tweak them as many times as you like until satisfied before you begin painting or making your stencil.

If you want to paint text or a bold image without using stencils, a neat trick is to draw or print it out in black and stick that piece of paper inside the shirt so that you can see it through the material and trace the design. This method only really works for white shirts, but with darker shirts you can use another trick – chalk. This is a little tougher because you want to make sure you apply it VERY lightly and you won’t be able to print it out from an image on your computer, but it’s a decent way to see how things will look before painting.

Work on a flat surface, like a kitchen table, and make sure you put plenty of newspapers down. Along these lines, also make sure to wear old clothes because this paint will definitely stain any material it touches (that’s the point right?). Have an old towel or rags handy and a glass or two of water to prevent brushes from being damaged by dried paint. Insert your cardboard into the shirts and get ready to paint.

If your shirts are not stretched by the cardboard or held tightly in place, use short, dabbing strokes to keep them from crinkling. When painting text, you may want to use a ruler to keep the letters from rising or falling down the shirt as you go. It’s also very important not to glop on too much paint because it may crack when the shirt dries, ruining your design. As with most painting, it’s a good idea to start with light colors and do the darker ones last. For spray paint with stencils, make one pass and let it dry a bit before giving the area another coat. Spray paint should ALWAYS be used outside or in ventilated areas.

Use a hair dryer to dry the paint a bit and then remove the cardboard so that it doesn’t stick to the inside of the shirt. Lay the shirts out to dry and go get lunch for an hour or so.

Setting the Paint
After the paint has dried it needs to be set into the fabric with heat. Place the shirt on an ironing board, paint side up, and cover it with an old towel or rag. Iron the painted area for 5-10 minutes on high (cotton) or whatever level your iron designates for that material. Make sure you cover the entire design or some areas will fade more quickly than others. Standard spray painted shirts should be hand-washed the first time, which will keep the paint vibrant for a lot longer. You’re finished!

Other things to consider painting are pillowcases, sheets, socks, or even underwear. Pillowcases are nice because this is the last thing your date sees before getting into bed and they’re the perfect size for a special image or note. And underwear, well…you can imagine the possibilities there.

For those of you who aren’t remotely artistic (like me), stencils provide a way to transfer amazing imagery to a shirt with minimal skills. You really just need to trace the outline of an image with an exacto blade. Seriously.

In a nutshell, you will need to find an image or drawing, convert it to black & white and print it out. Then tape a piece of mylar (plastic) to the front of the drawing and cut out all of the black, removing it from the mylar and forming a negative. The only tricky part is making sure you don’t have any islands, or areas that shouldn’t have paint but are surrounded by areas that do so were cut out. In this case you’ll have to leave a connector to keep the mylar together. After the negative is cut out, spray a little glue on the back side, attach it to the shirt, cover the rest of the shirt with newspaper, and paint. See the linked videos for more information; it’s much easier to understand when you see it done.

Stencil ideas can be anything that’s interesting or important to you, all you have to do is find a drawing or photograph of a powerful image and you’re halfway there. Well, maybe a third of the way there. Look at the videos in the Links section to see basic, intermediate, and amazing, but more advanced, options. Some ideas for subjects include:

  • Famous people (movie character, singer, inventor, athlete, politician)
  • Comic book character
  • Sport (surfer, snowboarder, windsurfer)
  • Animal (frog, gecko, bear)

Great stencil tutorial:

Another great stencil tutorial:

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If using spray paint, start out with dark colors on lighter shirts.


Paint $6/color
Mylar $1/sheet
Spray mount glue $5
Exacto blades $5

You'll Need

Paint (spray or fabric) or Sharpie
Brushes (optional)
Hair dryer
Old towel, rags
Glue, mylar, exacto blades (stencils only)


Regular t-shirt supplier
Alternative shirt supplier
Shirt painting tutorial videos
Stencil tutorial
Stencil tutorial

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