How do you plan to carry your "stuff"?
Anything that you carry in your shorts pockets is likely to fall out. If you wear a regular bicycle jersey, you will be laying back on it. I bought an inexpensive mesh photographer's vest. It has pockets for my wallet, cell phone, car keys etc and it's all easily accessible while I'm riding.
I sometimes wear bike shorts from which I've cut the padding and sometimes I wear gym shorts. A wicking t-shirt suits me fine.
A helmet with a visor would probably be better because the angle of your head is different. One thing I think you'll like is that you are much less likely to have sweat in the eye issues.
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My greatest fear is all of my kids standing around my coffin and talking about "how sensible" dad was.