The tip that was the biggest “aha” moment for me, and one that’s not been mentioned in this thread yet: that CLASSICS ALSO DATE. It just answered about a hundred questions as to why so many combinations of my outfits seemed really “off” when I thought I had the right elements there. The answer was that I was trying to marry a dated classic with current piece/s, and the whole silhouette just wouldn’t work.
And then it’s corollary, that IT’S ALL ABOUT THE RIGHT PROPORTIONS. So in any one fashion season, the change of one important element brings about the change of others, so the whole silhouette works. For example, skinny trousers brought with it fluid tops. Cropped trousers needed higher shoes to close the gap. For me, this explained why, in the years that I hadn’t been following fashion at all, it was so difficult to replace a single worn piece. This was because there was usually a whole new silhouette, a change that tended to pass me by, and the single piece of the old silhouette ( that I was trying to replace to go with all my other older things) was no longer sold in retail.