Thank you so much everyone!! Ok, I think I've got it, and it's a combo of recommendations. I think I will keep it simple for now with current classic partly because as Angie wisely pointed out, I do better with simplicity and partly because *right now* I'm trying to push just a smidge out of the comfort zone. Also, from a purely practical standpoint, when I search style words to get inspiration, comfortable returns a lot of loungewear
So comfortable will always come into play but for now I'll keep it bracketed - not eliminated though, as this really is important to me - let's call it "in the holding zone". Or as Sal says, when something feels off, it might be this element that is missing, so I can use for trouble-shooting rather than as a goal per se.
Thank you so much; this thread was extremely encouraging and insightful and I really appreciate every one of you!
Sally, I love relaxed and this is sort of a styling word I'm using right now - to get what to me reads as a current look!
Jessikams, my area is a couple years behind but the 'baggy pants' change has taken effect here, so I see far less skinny jeans and more baggy pants, even among my age group (the kids are ahead of course), which then means shorter tops, different styling, etc. So really it's just my area catching up to fashion, but because I am a mainstream dresser, it means it was time for me to update - not unlike what I did in 2010 or so when I traded in my bootcuts for skinnies, with all the downstream changes that triggered.