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1.
1) Used to describe a class of professionals who work in fields associated with information, creativity, social-media, etc. Derived from previous uses of "collar," e.g. blue-collar, white-collar, green-collar.

2) Anyone who works in the hipster economy, e.g. artisanal products, crafts, art related fields, communication, information, and anything having to do with memes.

3) Liberal arts majors who manage to get a job where they only wear ties if they feel like it, and with the top button undone.

4) Liberal arts majors who work in traditionally blue-collar fields.
Ex. 1
Hipster 1: "Winston just got a job at the Huffpo as a social-media coordinator."
Hipster 2: "Totally kewl, joining that plaid-collar workforce."

Ex. 2
"Dude, I forgot my rooibos tea at the new lunch-time yoga studio--man, I'm totally a plaid-collar worker."

Ex. 3
"So what's Mondragon been doing with that English degree since he graduated from Columbia?"
"Oh, he's in Brooklyn, making chairs out of reclaimed wood. Suuuuuper plaid-collar worker."
by Plaiddy January 07, 2013