For top if under 20 miles I will wear just a light colored tee shirt made of wicking material. Over 20 miles I'm a big fan of pearl izumi elite series. thermal jersey if under 70 degrees out.
Sport oriented boxer-briefs with semi-baggy zoic black market shorts (discontinued unfortunately!) Have never been a fan of padded shorts, maybe I just haven't used good enough pads. I have no problems riding 140 miles in boxer briefs and decent lightweight shorts.
I still use toe clips and love the adidas sambas originals shoe. Very stiff and lightweight, plus can walk around when off the bike. They last forever too.