Such interesting replies! I knew I could depend on that!
Jules, I think comfortable looks that are also current are a pleasure we should never deny ourselves. Especially if our lives are relatively casual. I was just thinking the other day that as the years go on, I would like to ALWAYS search for the "comfort" in "current" and gravitate in that direction. I'm sure you look fab in your BFs.
MRL -- hip to be square is tough for me, too, except unironically, I guess! Maybe I'm not really aspiring to that one. I do dress very practically a lot of the time, though, and I do wear gear for gear activities. Without shame. And sometimes incorporate gear pieces into my regular wear.
Carla, you are far from a C student. Your style has skyrocketed this year! That's very interesting about volume being a bit of a fear for you; I didn't know that. But you do look very good in classic tailored outfits.
Bella, you look terrific in both trousers and skirts. And I think skirts and dresses always enjoy more popularity in the summer. Or at least they do with me. I love them, but find them tough to wear in winter in my climate. It looks to me as if there are more skirt silhouettes available this season than there have been for a long while, so maybe you'll be in luck?
Rabbit -- interesting. I would say that the brilliant runway copy outfits you've experimented with have "just enough structure" for sure. And some of them have combined classics with trendy, although I guess in most cases the classic pieces were so simple (like tights, for example) that it might stretch the definition a bit. And I love the image you describe of that woman in the red rain boots, white shirt and jeans with nice bag -- it sounds a lot like combining classics with trends as well as irregular juxtaposition. I think that's the type of thing I'm after -- the confidence to wear what actually works in my climate/ situation even if it is a bit out of the ordinary -- but also to keep it very simple and streamlined. Without a lot going on.
Unfrumped, you're right -- irregular juxtaposition promises to allow us to shop our closets and experiment with what is already there . It's also a nod to thrifting, too.
Shannon, I think you've definitely figured out your "just enough structure" sweet spot, and it was a really interesting exercise to determine it. And you're right -- it's a matter of degree. Maybe I'm just not comfortable with too extreme outfit juxtaposition. I can take oversize, I can wear and love classics with trends, I can easily wear hi-low -- but it's okay if I limit my juxtapositions to the kind I've named. No need to jump on the seasonally confused bandwagon. I do think that juxtaposition is a really handy way of saying "current," though, especially for those of us who are past our youth. It's more unexpected in us, less "prim" and "ladylike."
Peri, you look great in your loose sweaters. And as an IT, you wear an oversize top extremely well. I think our tolerance for looseness and oversize fits truly varies. These type of looks simply don't flatter all figures equally; and then some people don't care as much as others about figure flattery. I always think if the fit on the shoulder is right, you'll rarely feel truly sloppy -- or at least that's how it feels to me, LOL. But like you, I seem to have a high tolerance for looseness.
Jewell, I'm with Rabbit - I'll bet you looked fantastic in the outfit you describe! I agree that family members can be oddly conservative, and if you just keep trying, they get used to the whole idea. That's definitely true of Mr. Suz.
Sarah, it sounds as if you are not alone in the desire for tailoring. I wonder if there is any correlation with body type and preference for tailored looks -- maybe Angie knows.
Texstyle, I think you hit the nail on the head; like it or no (and sometimes, I don't) my basic style persona is pretty darned classic. I love the idea of juxtaposition because it can erase some sense of stodginess or staleness. But if I feel like I'm in a costume, that's no good!
kkards -- you're slim, and I think it is easy for slim people to feel drowned in too much fabric. I look first to shoulder fit for the structure. But even then, on a slim frame, some looks will just overwhelm. I suspect Angie's suggestions about necklines are also especially helpful to slender people, and also the idea of scrunching sleeves, etc.
Sarah -- you're right -- boots with shorts is too seasonally confused and too young for me, I think. But it's worth a thought. If I could find the right shorts, and the right boots....
Thanks again, all! Interesting thinking this through.