I wonder if I am am judging that woman's face as part of the equation. She is not wearing any perceivable makeup and has an expression that looks like someone is showing her what they just stepped in.
Would I think of this look differently if she had full makeup and struck a more "fashionable'' pose? Maybe.
Those seemingly petty things like pose and makeup make all the difference between a pulled together, intentional look for a photo, and the impression of normcore/homeless/sloppy/caught off guard living life/ insert judgment.
So often I see such posed looks that, when subjected to life, kind of fall apart. A lot of looks look great in pics but are darned hard to maintain in the course of daily living. I try to look for things that stand up to actual living. This one may or may not - hard to tell. For all I know, if might be awesome in real life. I would not do those shoes, but the rest of it might be awesome and comfortable out in the real world.
