"Am I correct in that even with oversized, there is still very much a need to maintain certain proportions?"

Shannon, that's my feeling -- at least if one wants to achieve a certain level of flattery. I am finding out that, quite to my surprise, I like a slightly roomier, drapey top with slimmer bottom. It goes contrary to what I did years ago, but I think it's because I have now been taking pictures of outfits and am realizing that very fitted tops with fuller bottoms emphasize not only my wider hip but I think even more significantly the shortness of my torso, and I look very unbalanced. Slightly oversized tops in lightweight fabrications are working well for me because they extend my short torso and dont seem to shorten my leg line significantly (and I am lucky that it doesn't matter much if my legs look a little shorter than they are). The lightweight fabrics allow for movement and flow, which helps show a bit of the shape of the body underneath.

But if I go up to a boxier, chunkier top, all of a sudden I start losing the shape of my body completely -- I start looking like all of me is as wide as my hips and my shoulders (and boobs), and that is pretty unflattering on me.

That's my experience with achieving balance, at least. Now, since my thread on slouchy pants yesterday, if I somehow find slouchy pants that work on me and don't make me feel unbalanced, then I will really feel like I accomplished something!

Great perspectives represented here!

I'm a big advocate of wearing your clothes with confidence and attitude. Of course, style helps (nod to Angie) but I think one can pull off a lot with the right attitude.

As far as proportions goes, it matters what your goal is in dressing -- figure flattery? Emphasizing one area but not another? Exploring geometry? Different strokes...