Dear Lauren,

Kabbalistically speaking, a round challah speaks of the continuity of the life process; quite similar in meaning to the wedding ring. The braided, on the other hand speaks of the inter-twining of all of creation.

I would profess that, for the most part, it is a matter of custom stemming out of the various lands from which we migrated. Some preferred braided while others chose round. In my own household, while I was growing up, I never saw a round challah. Braided was the lechem of choice. Either, in my opinion, is equally "shabbisdik". We say "haMotzi Lechem min haAwretz"....we bless not so much the bread but rather the Source, Hashem, who placed the wheat into the earth for us to take it out of the earth.

Next Shabbos, be creative.........buy one of each and dip them into loads of honey.

Shalom