All this dress-up is to avoid being called a "Fred".

Read the Wikipedia entry on Fred http://en.wikipedia.org/wiki/Fred_(bicycling)

"Fred" is a derisive term used by road cyclists to describe other cyclists, usually male, that does not conform to "serious" road cyclists norms and conventions with regard to dress and equipment, and appear amateurish to them. The rare female Fred is a "Doris."

This style of fashion in the NYT supposedly will elevate the rider above the elite, as well as preventing the Fred tag.

But,

An interesting corollary for this type of Fred is that if someone is worried about being a Fred, he probably is one.

Whoever goes according to any expected norm is kind of a cog in my opinion. Every sport or hobby seems to have these expected dress code. The favorite one is cross-country skiers wearing knickers that end right below the knee. Which means you need heavier long socks or put on gaiters to keep your shins from freezing off. But gaiters are like upside-down pants. I say use whatever feels comfortable and conveniently isolates you from the elements.

People have a deep-seated need to be acceptable to the group they want to associate with.