Because who doesn't want to be regaled with the minutiae floating around in my brain?
That's what I thought.
DMs have two markets. One is made up of punks (original, true believers, and wanna-bes), and the other is trend-following youngsters. In the former, they are always in style (preferably the black boots). In the latter, they cycle through every ten to 15 years. So, if you think you can claim a punk mantle, DMs do not necessarily make you old. Me, I started wearing them when they were in fashion last time (early 90s) and kept wearing them up to about 2005 (old pair still in the closet, just not worn in a few years). Now that they're back, maybe I'll drag them out again, because you're right. they are comfortable. And we're old.
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