So I've been skateboarding for about a year now and I can do an ollie, but only on carpet or grass, or on concrete if I'm holding on because I'm afraid if falling. Will wearing knee pads, elbow pads and even wrist pads and of course a helmet make me less afraid to try it?

Wearing protection will increase your confidence as it will lower your chances of getting hurt but like the person above me said you won't know until you try it. So go for gold! nothing to lose everything to gain

yes but just a bit because it is all about your mind and am really shocked that it took you a year to ollie as my nephew is skating for less than week and he can ollie a curb

Yes the more the better.

Probably, only way to know is to try it!

You won't know until you try them.