Proper fit, harmonious colors and lines, and a controlled degree of modesty/daring appropriate to the occasion are what it takes for any kind of attire to look good. It doesn't work reliably if one merely attempts to follow rules like "no blue gloves" or whatever if one doesn't know how they achieve the goal.
Funny thing about that piece - it started out sort of philosophical, with some valid general points (or so it seemed), then it lost all credibility by its transparent eagerness to promote products and its obsession with James.
If you ask me, mix-and-match team kit and whatever socks you randomly pulled out of the drawer is totally appropriate for a morning pre-work-workout, or even an afternoon of hooliganism with a few riding mates, but if some former champion is in town for a charity ride, you might want to put on your "Sunday best." Sure, sometimes we really "don't care," but if we ever do, and we expect anyone to believe it, looking like we care is a practical necessity.