When there is a query about how an outfit looks, or K/R a clothing item, I often feel adrift due to not knowing anything about where the poster is trying to go but that that could be important. I realized that was a big problem in my own wardrobe collecting and I learned a lot from Angie's blog archives and some from WNTW on trying to have some focus. Also, having some fab outfits for "reference" as to why they seem to work and whether I want to duplicate them or say, like this but head more in this other direction. Then I might also be adventurous and say, I look best in this, but by doggies I want to wear some of that, regardless.
I think body type and fit come first because even though the style objectives may be classic or romantic or whatever, we may wish to interpret them for our body types, and most people want to look "good" as a basic condition. Let's say you love boho but don't look so good in loose stuff (not sure this is a good example, but it's a start, and boho is a short word! ). So the question is not just, does this look good on me, but could be, I want to really dress for my body type but I want to express my style in a boho type. So you might wear more fitted things but interpret the boho through prints, colors and accessories and very carefully selected area of "looseness."
So is fun and useful if when we get more about what a person thinks is her "best" or go-to looks, what direction she's going, whether a certain item or outfit is directed at that or is for fun or experimenting, whether a wardrobe item is a "place-holder" and need to be styled and utilized for now, and so forth. Let's say there's a waist-surrendering blouse that is not the most flattering in a particular photo, but then it might turn out that it is specifically to jump on that trend, or for a comfort-outfit or to try a new color or something completely off kilter from, does it flatter my body type to perfection. So the purpose of an item or outfit can matter as much or more than the first visual impression, but it might be important to know what the poster really wants from the feedback.
These criteria and details have been really great in some of Angie's posts about her intentional wardrobe acquisitions, dressing clients, and so forth. I'm trying to learn more about how to tell what issue or situation I'm trying to solve or meet in my own style and wardrobe and then at some point may be able to help someone else.