Doesn't the reference come in because the kids were playing D&D in the movie E.T.?

Yeah, with a line something like "I hope you fall in your portable hole."

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Granted, this will make you look like a bike messenger (is that so bad anyway?)

Yes...yes it is.

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It's pretty stylish, and still manly(ish).

You keep using that word. I do not think it means what you think it means.

Portable holes are from Bugs Bunny and The RoadRunner cartoon shows. (A)D&D may have them too (alas, I've forgotten much), but let's keep it original, eh!