Hmm... that is right, Suz. i appreciate your thoughtful comments.
I think I like the dress in part because it seems to fit my shape. A lot of dresses do not even if tried to tailor them. Me being a long-waisted pear-ish skinny top person. And the peplum actually "hides" or avoids super body con while still having a waist. So I was thinking that direction just seemed more natural than fighting it. But I continue to like several different "styles" I think and so maybe need to find what is the common denominator.
And some outfits I see with this or that length and this or that proportion do not look "good" to me even though others say, oh wow, how fab. So somehow I am not hitting the right fit between indulging my poison eye/ sugar eye and how to interpret for current styles--how can I have my cake and eat it, too.
I am trying to focus more on the thing or things that make an outfit updated but wouldn't have to fundamentally change some of the things I liked in the first place about it. You gave some great examples like a very on-trend handbag, and moira suggested footwear too.
An example I can think of is that if wearing a very unexpected belt--like zebra , or some punk metal/leather, or something--with the dotted dress--makes it look more like I "own" the style, that is the kind of thing I can see myself doing.
I might actually like some kind of oxford better than booties.
I am truly footwear-challenged despite having many shoes.
It is like Angie's comments about one classic piece but adding modern elements. Maybe first focus on what modern elements or trends I actually do love and see why don't I use more of that?
Then sometimes things that might amp the style quotient miss the point of the outfit, e.g., "wear that with a cropped black leather jacket" is great, but what about if you are trying to have a dress for warm weather!
Oh,poo.
Maybe I will try to post some more WIW type photos of other dresses and outfits and play, am I warm yet?