At first I thought this was about CaBI parties, maybe because I was out with unfrumped?
I never made it to the true skinnies party, in part because my legs are two sizes larger than my trunk and I feel the stuffed sausage look makes my legs look even bigger. Since I never got into tall boots (too hard to fit and my mild climate doesn't require boots), tucking pants into skinnies was never a concern.
As for boyfriends -- having the legs actually look loose is pretty much an impossibility for me. I thrifted a pair, but they aren't tapered at the bottom. I like them anyway.
Mixed media items always have me worrying about how they will wash/dry. I just got a top that is mixed media but doesn't really look it. The front is woven and the back is knit. Does that count?