We did a multigenerational trip back in 2012 and the topic of matching shirts came up, as well. It was something no one in the group had ever done before. Some loved the idea and some hated it. What we finally decided on doing was a similar theme, but not 100% matching. Our first thought was, since my daughter's favorite princess is Snow White and there would be 7 of us besides her, she could dress like Snow White and each of us would wear a shirt with a different dwarf on it. All but one loved the idea, but she was so adamantly opposed that we decided it wasn't worth it. We discussed different ideas and finally came up with one we all got on board with. We all chose a ride or attraction that was no longer in the park (Skyway, Superstar Television, Horizons, Snow White's Scary Adventures, Cranium, Command, Dreamfinder, and Disney Stars and Motorcars Parade). From there, we each picked out a baseball tee that was white with sleeves the color of our choosing. Then, the front of the tee had the words "Take me to (specific ride or attraction)" followed by the picture. Then, below that were the words, "Oh wait... (insert remark about it being gone)." We got a lot of compliments on them. We weren't completely matching, but it was enough for us.
For those interested, these were our comments:
Take me to Skyway! Oh wait... guess I'm walking to Tomorrowland instead.
Take me to Superstar Television! Oh wait... am I too old to audition for American Idol?
Take me to Horizons! Oh wait... It looks like Mars is the new Horizon.
Take me to Snow White's Scary Adventures! Oh wait... well, I would rather meet all of them at one time anyway.
Take me to Cranium Command! Oh wait... I guess there are just bats in the belfry now.
Take me to Dreamfinder! Oh wait... I never even got to meet him. (my two-year-old wore this one)
Take me to The Disney Stars and Motor Cars parade! Oh wait... Well, cheers for the premier attraction. Curtain up and on with the show!
We thought it was a good compromise. We had a set theme, but we weren't all matchy. Everyone seemed content. And it was fun to get comments from cast members and big Disney fans who remembered the attraction, got the references, and had fun things to say.