I'm glad you're comfortable enough to admit we often look silly, but still be ok with yourself anyway. It's true, we often look ridiculous and have terrible fashion sense, not to mention the fact that fetish clothes are so popular among CDers. And when this isn't the case, then we pass and no one is the wiser. Think about it, for every ridiculous-looking crossdresser you've seen, you've probably seen ten that you just assumed were women.
Also, we have to realize that it's really freaking hard for other people to understand why we like wearing ladies' clothes so much. Heck, I don't think even most of us know the answer to that. The way I put it, I have a strong female side of my personality that I need to express every so often or else I just can't stop thinking about sexy high-heeled boots... or something like that.