To answer your second question (re: handlebar tape) :

I almost exclusively use fizik tape or Cinelli cork.

As far as riding attire goes...

Warmer weather: in training rides/longer rides/fun rides: lycra bike shorts with a pair of baggy technical shorts on top, technical SS top; in tri races: tri suit
Cold weather: Technical tights under bike shorts, technical LS top, technical jacket
(Pretty much the same stuff I use for running, with the addition of the bike shorts)