Inspired by RunCarla's recent post about shoulder fit, and Torontogirl's following post on cardi fit, I find myself grappling with the idea of fit. I was "taught" that fit is very black or white - either something fits you properly, or it does not. It has been challenging to re-train my eye when it comes to fit - especially with tops and jackets, and the trending "oversized" looks. (Oh, and PPL, but that is a different post...)

Fit gets even more complicated, for me, when I consider different cuts like "relaxed fit", "classic fit", or "slim fit". Sizing up (or down) in a top or jacket often means the piece is only WIDER (or narrower), not necessarily proportionally larger (or smaller) all over.

How do you determine fit when it comes to oversized styling? What do you look for? Can you shop intentionally for oversized pieces, or is it a total crapshoot as to whether a piece will look the way you intend it to?