Gorgeous as ever, and I am touched that you included a tall boot outfit just for me in solidarity. I am still plotting how to style mine in some different ways to get them out of the closet after all.
#1 is amazing! No "poor man's version" at all! Although that jacket is a sort of taupey brown, the brown also has an olive undercast somehow...it is a bit warmer in tone, and works beautifully with the sweater and animal print belt. I love this on you!
#2 does not read as too dark to me and I suspect this vest is going to become a real workhorse for you. It is very trans-seasonal, which will give it a lot of opportunities for wear.
Waving at my sweatshirt twin. I was sick with migraine today and wore the matching pants to stay at home on the couch! I really love both pieces and use the sweatshirt frequently. It looks great on you. Like I said, an almost "lavender" grey.
#4 is so fun with the shoes. Love it.
#5 -- yes, I have this same problem with the seamed skirt I bought at the same time..fit is on the generous side and too straight. I quite like your outfit with the sweater -- it is a sort of sporty luxe because of the sweater's detailing combined with the bright red -- but I also think I see why it might not feel like your best.