Depends on where you wear the shirt. I think wearing it to a Lesswrong meetup would work.
I have a strong aversion to wearing T-shirts with clever slogans. After thinking about it for a couple of minutes, I think the reason is that there's no good way to filter the message: if a joke falls flat you can avoid making similar jokes, but a T-shirt just hangs around like a dead octopus in a Jacuzzi, slowly growing more awkward and obtrusive.
A LW meetup wouldn't be the worst place to wear that one, but I don't think one would be homogeneous enough that I'd actually be comfortable doing it.
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