Sort of. A few years ago we had a big blowout vacation to the Bahamas, and I wanted to do something special since it was to celebrate our DD's high school graduation. So I had an Etsy artist make a logo for the trip and put it on five shirts, each a different color. I liked it so much, I made another set of shirts. Then baseball jerseys. And wristbands. And glasses cleaning cloths. And pens. And, uh, lots of other things. I kind of went a little nuts. Everyone rolled their eyes and groaned and complained when I handed them out, and told them which days we had to wear our matching shirts on (it was a 7-day trip, with 3 "shirt" days).
But you know what? It was a big hit. Everybody at the resort commented on it, the employees all thought it was hilarious, and it kind of brought us together on the trip in a way that nothing else really could. This was with two teenagers and a boyfriend (now husband), mind you. It really made the boyfriend feel like part of the family, instead of this dangling hanger-on, and despite being way out of his comfort zone jumped in with both feet. You might say "it's not you" but as your children turn into adults, and new members join your family, it's nice to have something like that to help bring everybody together.
Now when we take "big" vacations, there's always a custom logo for that trip and everyone gets shirts with the logo in "their" color. We've since had a girlfriend/fiancee join us, and it has the same effect: there's something about getting "team gear" that helps them integrate into the group quicker and better than just saying "we're glad you're here." Teams wear jerseys for a reason, after all! And the group photos, as many have said, are awesome. And after a couple days, if you're alone walking around in your logo gear, you inevitably get a couple questions from other families or employees about your shirt, and you see people saying "there goes one of those Hulapalooza people!" It's like being a mini-celebrity.
So, don't knock it 'til you've tried it. You're on vacation, and you don't have to look "cool" to everybody. Look dorky, and let them make fun of you, and remember that you're not here with all of those other people - you're here with the rest of your team. That being said, I don't know that every day makes sense - I always leave a little more than half the days for everybody to wear whatever and express their individuality.
