Theme Park Style
Fandom Shirts
I have a Callahan Auto Parts t-shirt, and any time I wear it at the parks, someone points and says something like, 'hey, nice shirt.' I've owned three of those shirts over the years. I have a tee where a rabbit/duck sits on a 2D grid. Which one you see depends on how you read the axis. It catches people's eye, and I've gotten a couple of "you broke my brain" comments. I actually own two versions of the shirt and did a swap halfway through the day to mess with my niece. She caught on.
And you don't have to buy a shirt either. I got my wife a Cricut and she has made a couple really awesome shirts. But if you want to support the site and walk away with something fun in return, our merch shop is basically a tip jar you can wear.
Bags
My wife has two Loungefly bags, each a gift. I got her a Goofy Movie bag with Goofy, Max, and "the map" prominent on the bag; a friend got her a Tangled bag that lights up at night. Cast members and guests sometimes come up to her and say, "I like your bag." We have keep count on who got more feedback in a day. One time on Main Street, a cast member randomly gave her a button because it was their favorite bag of the day. We try to reciprocate when we we see people with fun merch too as long as it's not super awkward.
The 10L Packable Daypack has been my wife's favorite of late. No brand IP. Just something large enough to fit disposable ponchos, smucker's uncrustables, and our two water bottles.
Security Checkpoint Tip
Bags get people taken out of line and put into the second security line all the time. Take things out of the bag — things like your battery recharger — when going through security, so they're in your hand instead of buried in your bag.
-Aaron