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eli_sennesh comments on You have a set amount of "weirdness points". Spend them wisely. - Less Wrong
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I agree with the general gist of the post, but I would point out that different groups consider different things weird, and have differing opinions about what weirdness is a bad thing.
To use your "a guy wearing a dress in public" example - I do this occasionally, and gauging from the reactions I've seen so far, it seems to earn me points among the liberal, socially progressive crowd. My general opinions and values are such that this is the group that would already be the most likely to listen to me, while the people who are turned off by such a thing would be disinclined to listen to me anyway.
I would thus suggest, not trying to limit your weirdness, but rather choosing a target audience and only limiting the kind of weirdness that this group would consider freakish or negative, while being less concerned by the kind of weirdness that your target audience considers positive. Weirdness that's considered positive by your target audience may even help your case.
This carries the slight problem that people tend to get offended when they realize you're explicitly catering to an audience. If I talked about the plight of the poor and meritocracy to liberals and about responsibility and family to conservatives, advocating the exact same position to each, and then each group found out about the speech I gave to the other, they would both start thinking of me as a duplicitous snake. They might start yelling about "Eli Sennesh's conspiracy to pass a basic income guarantee" or something like that: my policy would seem "eviler" for being able to be upheld from seemingly disjoint perspectives.
Right, I wouldn't advocate having contradictory presentations, but rather choosing a target audience that best fits your personality and strengths, and then sticking to that.