I would plan on wearing whatever you're going to ride in on the swim (unless you're going to throw on a simple grass skirt). Otherwise you're going to be trying to pull on a tshirt over wet clothes. It'll be frustrating. You want things to go as smoothly and simply as possible. Fighting with clothing isn't good.

Here are some sites for race day checklists:

http://triathlon.racechecklist.com/ (This one is WAY involved)

http://www.beginnertriathlete.com/Do...0checklist.pdf (This one is much simpler)

http://go-adventure.com/tnt/document...nChecklist.pdf
(This is another simple one)

If these don't work for you just Google "race day checklist". There are a ton of them out there.

I like printing out my checklist and then checking off what I need to make sure I have it all. I hate leaving stuff out that I need.

When you set up your transition spot put your bike stuff together and then your run stuff together, separate from the bike stuff. You don't want to have to think about where everything is or have to sort it out in the middle of the race. You can just sit, or bend down and grab what you need in one swoop. I put my bike stuff on one side of my towel and the run on the other.

You don't NEED a race belt, but I find it easier to have my number on the belt so I can grab it and put it on as I run out of T2 than having to stop and pin it on my shirt.