This post about wearing hijab is really very thoughtful, while still being an easy read. I think a lot of it holds true for Jewish (married-woman style) head covering too. Here's my favorite line: "Although nobody on the outside could see my hair, my appearance underneath can still hold as much significance as I want to give it." My image of myself is both ways that I see myself in the mirror- hair covered (in all its different silhouettes) and uncovered and loose and down past my waist. It's as important to me as it ever was- even if none of you ever see it again.
The other thought I wanted to draw out is "I choose who sees what’s under there and that gives me a sense of power and reassurance I wouldn’t trade for anything". Clearly, it doesn't speak so much to wearing a kippah, but it's an interesting set of ideas to think about. Much of what's said could go for any modesty practice, but there's something about choosing to cover a part of the body that isn't in the secular vocabulary that is particularly vocal- especially, for me, in speaking to myself. It's a message that I hear most from my head covering, far more than the rest of my modesty-fueled clothing choices.