Great insights, Shannon.
I've almost entirely stopped pure "thrifting." I still do go to the consignment store and to my amazing vintage store in Toronto (though I've only actually made purchases there once.)
I'm finding that the items I buy on consignment are very hit and miss - which is one reason it's hard to stop going, in fact! This past season I bought my fuchsia silk suit, a black cotton top, my Marni-esque full cotton skirt on consignment. The suit "cost" $20 or something, and the skirt and top were "free."
The suit was tough. I never wore the trousers (and didn't bother paying for alterations as I just didn't think it was worth it). I wore the jacket maybe 3 times. (It's just not the right cut for me, gorgeous as the colour and fabric are). I did wear the top at least 7 times, however, and for $20 I guess it all evens out in CPW and JPW (love that new acronym!) Especially since I'm pretty sure I'll wear that top again next year.
Meanwhile, the skirt and top were TOTAL wardrobe workhorses for me this summer. I wore each of them at least once a week.
It's finds like that, that make it tougher to give up consignment shopping!
But let me talk about sales. Sales in regular stores, I mean. They remain the bane of my wardrobe existence. Again, I find some good stuff. Stuff I really enjoy wearing. And I do find that I'll sometimes experiment with a new colour or cut at a sale, whereas I still hesitate to do that if an item is full price and I'm unsure about it.
And yet....by and large, the stuff I don't wear much is the stuff I've bought on sale.
My main trouble, though, is that I'm just not as good a planner as you are. You seem to have a very clear idea of what you need. I feel totally in the dark about this. I honestly have no idea, even after making list after list after list. I'll pull things out, try to imagine outfits, put the stuff on....and I STILL don't have a very clear grasp on what my holes are. I think this comes from years of absolutely ignoring fashion. I wore a T shirt and jeans and that was it. A sweater if it was cold. So how would I know what I would need to make an outfit? Know what I am saying?
I'm starting to think that in addition to thinking in terms of item/outfit/capsule I need to think very, very specifically in terms of THIS (or that) PARTICULAR OCCASION. What will I wear to workout in in June? How about November? What will I wear to this afternoon presentation in September at the Seniors' Residence? What will I wear when I'm working at home, sitting on my saddle chair but meeting remotely with colleagues? What will I wear when I go to lunch with my super-casual friend? How about when I meet my poet friend for drinks at night? What about date night with hubs? Or when I go on this or that trip?
It sounds ridiculous, but I am beginning to think that for me, it's truly the only way. Otherwise I still end up with a lot of boring basics (some of which duplicate other basics), a lot of subpar essentials that don't necessarily work together (because I buy them on sale instead of recognizing that these are the core of my wardrobe and deserve a bit of attention), a few (very few) statement items....and almost no sense of my own "signature."