While I mostly work with photography, I recently designed a T-shirt for our family reunion. I'm not a big Illustrator user, so this took some time, as I had to learn how to use it as I designed! But, I'm pretty proud of the end results!
Front: My Grandpa, Louie, told his friend/brother/cousin (I'm not sure about this part) that he was going to go to the Shiloh Peach Farm (that my Grandma's family owned) to pick a peach and make a pair... When he talked to my Grandma, and asked her to marry him, he told her that he wouldn't be happy till there were only 26 letters in the alphabet; till u and i are one... yeah, he was a slick one :)
My Grandpa passed away earlier this year, in April. They would have celebrated 60 years of marriage in June. While he (and the rest of our family) consider an engagement to be just as permanent as marriage, just as much of a commitment, we made these as tribute shirts, as they had definitely been married via engagement for a full 60 years.
This is the back of the shirt. I had to make several different versions, and on the one that I happened to have saved on this computer, there are 2 names missing ( I told you I was still learning! I'd deleted a line by mistake)... but, still, you get the idea. It's our Family Tree!