I am going to say something silly:
Something old
Something new
Something borrowed
Something blue.
Yeah, every day is a wedding around here.
But in all seriousness....
I used to have more of a retro element to my style. I don't as much, these days, yet I do still feel most comfortable when I'm wearing at least one classic item -- whether that be a blazer, a button up shirt, a pair of jeans in an iconic style...etc. That takes care of something "old."
Something new...Like Caro, the older I get, the more important it seems to me to pay attention to trends and selectively adopt them. I feel best and most myself when I have incorporated something very modern and current into my outfit.
Something borrowed...a big reason I'm here on YLF is for inspiration. This is one way I learn about trends and figure out ways to adapt them for myself. Borrowing is beginning to feel natural. I also borrow from nature, from the weather, from my mood in figuring out my outfit for the day.
Something blue...well, if you look at my closet, it's all there! Blue is both my dominant neutral and my dominant colour. I don't know what I would do without it in my wardrobe! I wear it summer and winter, in items from PJs to workout gear to formal wear to denim. It's so me.
Great topic, gryffin. Thank you for the spur to thought!
ETA: I also wear contacts or glasses always (except asleep). And mine also cost a fortune. I have two pair of specs anyway and so far have found them worth the CPW. But I hear you. I wear progressives, am low vision, also have astigmatism, and am a real pain to fit with frames for a whole variety of reasons. So...yeah.