Preamble: I am a rabidly reform, off-the-deep-end Jew. I have chosen, also, to wear a talit katan every day. I hate kippot.

Amble: It seems that no one quite knows when Jews started covering their heads. It is not mentioned in Torah. It is not halachah from Talmud either. The earliest example of a Jew expecting another Jew's head to be covered, comes to us from the Responsa of Rebbe Yehuda of Italy. He received a letter (in the 16th cent, I wanna say, but don't quote me on that) inquiring after why he did not keep his head covered. His resonse was, "Cham li." He actually responded be telling the writer that he was simply hot. I take a similarly flip attitude towards it because the various reasons, including the one cited in the wedding announcement, have never seemed compelling enough. Tzitzit, however serve to set me apart, like our edgy groom does with his kipah, and I have the added bonus of knowing why I wear them.

Postamble: I really hate wearing a kipah. 

Firstly, the research I've done (which, unfortunately, doesn't include reading any of Talmud myself) says that the covering of the head is in Talmud. One of the sages told of his mother not allowing him to walk more than 6 cubits without his head covered.

Second, how do you keep your shirt tucked in while wearing a tallit katan? Every job I've ever had has required me to wear my shirt tucked in, and considering I can't even find a job that will give me off for Shabbat, I doubt I'd find one that would allow me to wear such a thing.