I voted cute of course because we did it on our trips, two to Disney and one to Sea World. On our first trip we had 3, one for Chef Mickeys, one for Crystal Palace and one Thanksgiving shirt. On our Sea World trip we matched on each of our two touring days. Got lots of compliments on those.
Our last Disney trip I went all out. I went overboard a bit according to my daughter, but every time I was looking through designs she would jump on the bed next to me and end up saying I dont know how many times, Oh, put that on a shirt for me! We went for 10 days and we each had a shirt a day, but not all matching. We had 4 shirts that completely matched, one for Epcot, one for Tusker House/Animal Kingdom, one for Crystal Palace and one for Garden Grill. The other shirts were made from designs here, but we werent matching each other. Usually the shirt of the day represented something we were going to do that day. Like dd wore an Ariel shirt on the day we planned to do the meet and greet. Actually she and I matched that day. When we had our princess character meals, I wore shirts that had princess themed name fills that said Mom or Mama. Ds wore a Handy Manny shirt the day we had our Hollywood and Vine breakfast at DHS and dd and I wore another type of shirt. Ds had a Mickey shirt he wore to Chef Mickeys.
No shirts in the plan for this trip at all. Although I may do one for our 2nd park day. I scored an 8:10am Crystal Palace ADR and it might be neat to have matching shirts for those almost empty park Photopass shots. Other than that, dd has a couple of special outfits and ds has a couple of Disney themed short sets, but thats it for now.