Interesting thread - I love these threads that go in a few directions.
A couple of comments and observations;
Approprio - I have never heard that. "Cool" is a commonly used word here - as in "Your new haircut is cool", "That was a cool party" or even, as an affirmative answer to the question "Shall we meet at 4pm?". I have never heard of it having negative associations - it is possibly a bit overused and ubiquitous and as with lots of words, it can mean different things. It can mean an edgy sense of style, or someone who has that X factor, but it can also mean "That was a fun/happy/awesome night" or "Yes 4pm works".
Where it can be disparaging is in the statement "Oh she is in the cool crowd" - in a school situation for example.
Some people do have a cool, "not trying too hard", fun edge to their clothing... but it is such a hard concept to pin down. Being cool in your dress to me shows a lack of affectation - not showing too many brand names or too many trends at once. And it is a style that appeals to me more than the Real Housewives style (to take the opposite end of the spectrum).
None the less I like the sound of the direction you plan to take Krish and think it sounds a fab style that I hope to adopt too (in my later 40s - or does 47 still count as mid 40s).