Bibs

Ah, cycling bibs, one of the best litmus tests of how far your cycling addiction has progressed.  You start off just wearing normal 'gym' clothes, because, hey, WTF, I don't need no stinkin' new clothes, ya jamoke (for purposes of this discussion you are a Jersey guido).  Then, once your ass becomes a wasteland of soreness you either
A) scale back cycling, since it's for queers anyway or
B) buy some cycling shorts, most likely the cheapest pair available from Performance or Nashbar.
These suffice for about, oh, 32 minutes until you realize they are made from a combination of steel wool and hay, held together with staples and a chamois made, apparently, from old Juicyfruit scraped from the bottom of the factory breakroom table.  So you decide to upgrade, once again, and you figure, what the hell, I already look like a freak, my family is embarassed to be seen with me in public, why not go all in and wear a 1930's bathing suit as well.  So you buy some bibs.  Maybe you've learned your lesson (or at least your taint did) and you buy a pair of Pearl Izumi's from your LBS.  And for many this is the pinnacle of their cycling trouser evolution.  But some of us go farther yet, exploring the upper regions of the cost spectrum, shelling out hundreds of dollars, our spleen and a child to be named later for a pair of Assos, which according to their reviews in Bicycling will make you faster, skinnier, more attractive and, for some unknown reason, able to paint amazing watercolors of tulips.  Eventually, with lots of pain, suffering, monetary outlay, and a bit of luck you find a pair of bibs that is comfortable, moderately affordable, and doesn't make you look like a total freak.  Alright, they all make you look like a total freak.