Are you an experienced air-traveler? Help the "rookie"!?

I will be on a short domestic American flight, one "carry-on", and one connecting flight. Do I really have to wear a sweat-suit and flip-flops in order to get through security successfully? Taking my very first flight tomorrow, and would prefer to skip the "cavity search" if at all possible! I have consulted the TSA website as to all the prohibited items but they do not tell you certain things. Like medications. Can you bring "gel-cap cold-medicine" as long as the carton is not opened for instance, or do prescription medications delay the security screening process? Help! I want to wear my jeans and my boots (they do zip up...no sweat!)