functionality is my highest priority. i will invest in comfort but not snob appeal. i wear bike-specific shorts, SPD touring shoes, and layers of t-shirts (depending on the temperature) topped with a light windbreaker. over the windbreaker i wear a reflective vest for visibility, which is a lot more eye-catching than almost any cycling jerseys.
to me the cycling jerseys look pretentious, and cotton t-shirts do perform just as well (if not better) in wicking moisture. plus with the reflective vest i can wear anything and still be very conspicuous in traffic.
i have lots of friends who wear cycling jerseys and make fun of my t-shirts and construction-worker reflective vest. but i don't spend $60 on my shirts, either, so the good-natured ribbing goes both ways.