Stretchy waistbands for a desolate wasteland

At what point does one simply give up? This was the question scuttling through my mind as I rode the bus to school today. There was a guy sitting across from me. He looked to be wandering through the desolate wasteland that is Provo at age 27-30. No ring. His attire consisted of old, utterly non-flashy Reebok cross trainers, an old Levi jacket with the sheep wool collar, and cheap Wal-mart/K-mart-esque jeans, the color of which I have seen only once (actually the color of a pair of diesels I own, that I can usually only bring myself to wear about twice a year, some kind of weird blue). You know the type, the jeans that really aren't made to fit anybody, and unless you have a square ass you could never fill them out. Baggy, and uneven. To top it all off, the jumbo-tron beanie that you wore in elementary school that made your head itch as though you had a plague of lice, which your parents bought you because times were tough and they didn't want to spend more than a dollar. Probably blue. Now, you may be picturing someone ugly. You would be wrong. He was a decent looking guy. But as he sat there, pulled off his beanie and didn't bother to fix his hair that was sticking in several unnatural directions due to the immense amount of static those beanies create when removed, he looked defeated. His clothing and demeanor seemed to sigh, and say, "Meh. I just don't give a damn." Now, don't get me wrong. I am the last person on the planet to spend $200 on a pair of jeans. In fact, most of the time it would be difficult for me to be wearing more than $40-$50 worth of clothing all together, including shoes. But at what point does one simply give up on style all together? I thought it was after marriage that one could legally wear dad pants, but apparently in that sad, lonely, demoralized slice of life between 27 and 30, comfort is king.