I may look like a tourist, but oh well...
head to toe:
if hot outside
-sunglasses
-a Disney shirt picked out for the day, depending on park
-black Tink lanyard w/pins & pouch for cards
-cellphone holster
-black wicking fabric yoga capris
-teva sandals w/arch support bandages
(dbf carries camera & water bottle attached to his shorts. if he isnt with me, i will wear bermuda shorts w/belt loops to attach the camera & water bottle)
if cooler outside
-yoga wicking fabric pants (or jeans if really cold)
-one of my mickey hoodies
-toe socks w/my teva sandals
and the above shirt/sunglasses
I have a small cross-body Lesportsac bag that i have used but i really hate bag check so it usually stays home
I try to be as comfy as possible!
I think I am going to have to look into the wicking clothes you talk about. I chafe really badly, and even with body glide and anti-monkey butt powder, I still chafed some. I used moisture wicking socks, and they were fabulous, but never thought about clothes that do the same thing. I am not used to sweating like that, and since I have to fit all my clothes to my waist and chest as they are the biggest parts of my body, my clothes are ill-fitting in every other area. They rub, rub, rub. I even turned my pants inside out one day to avoid the seams rubbing me. It didn't help, AND I looked like a dork!
I would love to figure out how to go bagless in order to avoid bag check. Since we will have a stroller I'm thinking about just stuffing the "kid stuff" underneath.
I tried this and then remembered since we were using Magical Express, we had to be able to fold the stroller. That required taking everything out. If you are using your own car this won't be an issue of course, but for us it was terrible. We ended up just sticking with throwing our bags into the stroller and hitting the bag check. Next year we are doing small backpacks for everyone to distribute the weight. We need to get used to not having a stroller to throw our junk into!
As for me...
I went total Disney Dork in 2011!!!
*No hat b/c I can't stand them, but I used spray sunscreen dusted into my hair to keep my color from fading.
*Every day we had different homemade Disney shirts to wear. We did: Single Mickey head tie dye shirts, Triple Mickey head tie dye shirts, family vacation Mickey shirts with our top ten reasons for visiting WDW listed on the back, Epic Mickey spray dye shirts, Star Wars Weekends shirts, and then I created my own Linked Mickey heads shirt, bedazzled Mickey hiding in my pocket shirt, and hidden Mickey shirt.
*Capris or shorts
*Moisture wicking socks, Nikes for part of the day, Crocs for the rest
*a Mickey bag that could be worn over the shoulder or around the waist. Sort of a non-fanny pack.
*I gave in to the pin trading, but compromised and instead of a neck lanyard, went with the hip lanyard.
*a clear pouchy thing that clips to my shirt, pulls out when I need to show my KTTW, and retracts when I'm done. It was awesome.
*And on day one I sport the required Minnie ears.
I wasn't "hot" for sure, but I was as comfy as I could be (my chafing was much improved from 2010), and I had fun. I'm sure I'll be even dorkier this next year. I wear a gi most of the time anyway, so stepping off the mat and into my Disney world is awesome.
At least for a few days... I love to frame vacation pics and hang them up in the house. From head to toe...
). If my shorts don't have pockets that zip or button closed, then I'll carry a Vera Bradley mini hipster. 
Last time I went with capri pants, Crocs sandals, and an entirely too big Vera Bradley backpack (though to be fair I had a barely 2 year old and all her stuff). I love my Crocs, but after about 5 days I really wanted something soft and cushy on my feet. So, for our June trip I'm leaning toward:
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