My response is kind of generic so maybe doesn't address your particular situation in a really personal way.
Maybe it is more about being sure one is dressing for one's sense of style and fun and that that comes through. As opposed to dressing to compensate for things that aren't real. As in, lots of folks have been indoctrinated that they can't wear this, or that, due to body shape, or hair color, or age, or whatever, or are embarrased to think in terms of trying to be pretty--lord, who would even try, if we used the fashion models as our only yardstick.
And then within that, seeing if there are "message" goals (modern, sophisticated, playful, professional, approachable, or many others) that are also coming through.
So if I think about a style change or evolution, I hope it's not just to please someone I've never met, but more about getting more and more in tune with my style, my stage in life, what's fun about fashion, and learning what really works for me or doesn't.
And if I look for feedback on outfits, I might or might not agree but at least I get feedback about how it looks to someone else and I can take that into account. Hence the whole concept of whether one is finding achieving "my style persona" and at what point I may decide to shift it this way or that.
So for example, generic advice of "just be yourself" in fashion no matter what isn't really the modus operandi here or no one would ask for K/R, or advise to try something longer or shorter, and all of that--it's about fit, proportion, figure-flattery, color beauty, and then trends, dated-ness or lack thereof, effortlessness, chic-ness, and the whole "ensemble" as Angie describes.
Well, I guess that's no help!