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Metus 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.
To make this picture a bit more colourful: I love suits, they look great on me. But I will be damned if I wear suits to university for people will laugh at me and not take me seriously because to the untrained eye all suits are considered business suits. On the other hand hanging around in a coffee place at any odd time of the day is completely to normal to the same group.
Contrast this with the average person working in an environment where they wear a suit: The suit could help me signal that I am on their side, the being in a coffee place at any odd time would then become my cause to be accepted.
The lesson then is to pick the tribe you are in, as you will know their norms best and adher to them anyhow, and then a cause that will produce the most utility within that tribe. It just so happens that there is the extremely large tribe "the public" which sometimes leads people to ignore that they can influence other, really big tribes, like Europeans, British, Londoners and then the members of their boroughs, to make a divide by region.