I had to post this asa big Thank you To Angie. On @LisaP's thread about new purchases, Angie recommended trying the boots on with different outfits, and determine what fits into her style for the next 3-6 months.
Having recently bought a couple of pairs of black boots to fill a wardrobe hole as well as a pair of pants I wasn't sure about, I decided to follow her sound advice and devote since time to trying on the boots wth all my pants to decide which pair to keep.
I had bought a hight heeled black leather bootie and a high heeled suede sock boot to replace my aging black pumps which I rarely wear anymore. I knew I needed black boots, but I want sure I needed both. Usually I would let them sit in the bag and then pull them out hurriedly on a weekday morning to try on with whatever outfit I was wearing and hope they worked. This time I tried them on with every single pair of pants I owned (a LOT, Mostly thrifted) to see which pair went better wth my pants.
I had a mini revelation. A couple of years ago, I wore skinny jeans almost exclusively, which made boots relatively easy - booties, heeled or flat, long boots, heels - everything served to go fine wth ankle cropped skinny jeans.
Having moved away from jeans last winter, I now have a wide range of pants - wide leg, narrow leg, slouchy, ankle length, full length, culottes. And trying them all on, I realized - a different pair of shoes and boots was needed for each. And if I want a luxe look and I'm concerned with proportions, I need to make sure I am wearing the right ones.
So I opened up my style book app and wrote down which shoes and boots went with each pair of pants. There was actually a need for both boots I got - the sock boots went well with cropped wide pants and longer full lengths, while the leather booties went well with skinny ankle pants and jeans.
While I was at it, I tried on my cropped blazer with my fuller wide legged pants to see which proportions I liked best. And I test drove a pair of pants I wasn't sure about by making several outfits wth them (including the boots to go with them!)
The whole process took me a couple of hours, mostly because I have so many pants (around 30.) But it was SO, SO useful. No more running around looking for shoes that go at 7:30am when I am already late, hauling several pairs upstairs to check in the full length mirror! Now I'll just refer to my stylebook app to know which shoes go. Angie was right - a couple of hours invested up front had made me sure about my purchases and saved me time in the long run.
Angie, you are probably smacking your forehead saying "I've been telling you this for YEARS!!" - but it finally sunk in. Thank you