Lyric discussion by kagi 

Cover art for Sackcloth And Ashes lyrics by Mr. T Experience, The

I think you guys are missing the point. It's not about materialism; it's about self-confidence. Sackcloth and ashes are traditional symbols of penance (in the past, monks would actually wear deliberately chafing garments to punish themselves for their worldly sins and prepare themselves for God). This is the joke of that line about "the silly habit you've put on" -- both a figurative monk's habit (clothes) and a behavioral/psychological habit (relentless self-accusation and despair). It's also the joke behind the line about "she's not sorry for her sins / as long as she looks good" -- the girl is not in the same self-punishing mindset as the boy here.

So here's the setup: boy, after a breakup, is going around feeling like he's totally worthless: "sullen and regretful, querulous and fretful, carrying a head full of evil thoughts." He meets a new girl, and it's the right girl, in the right place, and she's totally hot and fun, but he's too messed up to be able to go for it; he could only be "someone to feel sorry for," and she's not into that. So until he comes out of his depression, he's not getting any. (Corollary: it's easy to get another girlfriend when you already have one and you're feeling confident, but really hard when you're feeling lonely and rejected).

@kagi Not the hero we asked for, but the hero we needed!

Great explanation.