One of my favorite blogs, College Prepster, did a tutorial on Monogrammed shirts inspired by The Frat Collection. We took her instructions and improvised… and our pocket tees were born. 
Forgive my iPhonetography. 

What You’ll Need:

Iron On Adhesive: I used Heat’nBond Ultra Hold
Pocket Tees: I used Fruit of the Loom. Side note: Target doesn’t carry these in-store and Walmart doesn’t carry Men’s size small. Online may be your best bet!
X-Acto Knife: I have a bunch of these laying around. Find them here. Especially if you don’t own fabric scissors. Side note: You’ll need a thick surface to use your x-acto on. Cardboard boxes work well! 


Following CP’s tutorial, everything went off without a hitch! 
White fabric doesn’t work well as the pocket base, iron-on adhesive shows through. I printed out the letters first, then cut them out, then traced them onto the iron-on adhesive. For Libby’s ‘ERM’ pocket, I used the font Muncie (free!) and my ‘KDM’ pocket I used Abraham Lincoln (also free!). 
If you want your iron to be around past this project – always make sure your fabric is wider than the adhesive. Heat on the adhesive will result in a sticky, useless iron.