I totally do this and we have a blast with it!

I feel not an ounce of shame, over the years we have so many extra magical moments because of it.
My kids are now teens and they still want to do this because it is now tradition. Now I can't get them to wear the stuff they did as kids, but we match our shirts thanks to the lovely ladies on the Design board. The flip flop on my avatar I just made to match our Esty zebra Minnie shirts. I am making matching flip flops for all the girls. I have to make 90+ shirts for this upcoming trip and have to make at least 5 sets of flip flops.
First trip DH refused to match with me and our 3 DD's but people gave him such a hard time..."where's your green?" Where is your matching shirt?" and so on and so on. After that he gave in, and even convinced his family one year on a GG trip to do it with us. We all did it and it was fun...even the most reluctant of our group ended up having so much fun, they bought DVC after our trip and he was not even a fan of Disney!
We are even bringing DD's BFF and she is going to match or not come

No she will love it! She has never been to Disney before and has seen our pics from past trips and said she would love to match. It is a surprise trip for her, so hopefully she was telling us the truth

We are all wearing birthday shirts, celebrating her 1st Disney Un-Birthday. I can't wait...color me an estatic Dork, to me Disney is just different and I do a lot of things there that I never do anywhere else. I even got a shirt for DH- What Happens in Disney Stays in Disney!
Love matching and proud of it!
I have all my shirts mapped out for each park, this makes for great pics. In the past I also have had us wear special matching sets for character dining or Poly Dining too.