50th wedding anniversary t-shirt ideas?

I can't say for your family. My parents would neither one ever wear a printed t-shirt. It just isn't their style. What would you put on it?

I think having a photographer create a family photo would make a better keepsake for everyone.

For your parents, a photo book with photos from over the years would probably be much appreciated. I did my parents 50th and we did a party here locally. It was not a surprise in that they knew about the party, gave me the guest list (good thing because I was about to invite a woman my mother can't stand - who knew?) and approved the menu. I did the entertainment and decorations as a surprise. Part of the decorations consisted of poster size photo collages of black and white photos. I had them printed at Walmart and everyone loved seeing them. This also gave me the opportunity to get the family photos scanned and backed up. I've since used some of the photos for minibooks for each of my parents for birthday gifts.

Personally I am not a fan of matching tee shirts. In addition I hate regular boxy tee shirts and much prefer a shirt that is designed to flatter my body. For me it would be a waste.

Family photo yes! White tops and kakhis, not unless we are traveling back to the 90s.