The last time I wore the Chester Molester jacket was nine years ago, when I was a "salty" Third-Phase recruit at MCRD PISC. Prior to that, we had to wear the Mothers-of-America-issued poncho, which not only let the rain in, but kept you wet with sweat. For those of us who "rated" to look like Inspector Gadget with Kung-fu Grip, it was a symbol that we "made it."
Anyway, though I haven't worn it since then (aside from the occasional inspection, INCLUDING the one at TBS), I still have it because it is a required uniform item.
Does it suck dropping $150 or so on a uniform item you will never wear? Hell yeah it does. If money's an issue, buy one from a thrift store on/near base, or go to Quarter Sales at either of the Recruit Depots. It also sucks to drop a few Benjamins on the other required uniform items we rarely, if ever, wear or use (particularly in aviation), such as the Wooly Pully, the Mameluke sword, six pairs of utilities, the green barracks cover, etc. However, we all knew how much it was going to cost before we raised our right hands and signed on the dotted line.
Call me old-fashioned or naiive, but if the order says, "Officers will procure and maintain, in good and wearable condition at all times, the uniform items prescribed...," then I do it.