[Dylan16807]

>What's wrong with enjoying the feeling of being counterculture?

In terms of a stereotypical hipster, it's because it's being smug that you're not following the crowd. But you get there by paying a lot of attention to what the crowd likes, and using that as your primary decision maker. AKA you're following the crowd.

It's okay to like being unique, but find a niche though your own preferences, not though hypocritical reasoning.

[comrade_ogilvy]

I suppose there is a kind of self-contradiction is trying to be "fashionably unfashionable" which seems ripe for mockery.

But, in practice, the mockery boils down to an exercise in More Authentic Than Thou based on guesses from superficial details. Isn't making judgements about authenticity based on a few superficial details an even more loathsome exercise in hypocrisy?

I do like EvanKelly's point here: "What is there to be genuine to."?

What the heck is someone supposed to wear that is neither an overt exercise in conformity or a contrived exercise in non-conformity? What would in between or opting out of the pretense look like?

In fact, it might look a lot like Mr. Hermelin, whose clothes look functional and cheap, without any visible labels, without any apparent in-factory distressing of the fabric.