OK, so I ordered the Transcend and the flares. I'm growing concerned over dye transfer from the jeans to my shoes.... especially since most of the shoes I want to wear are suede. UGH why do I keep buying suede?!?! Anyway, I will have to research a fix if the jeans fit. The boots I wanted were sold out, so I added a dressy metallic sandal to try, since my only sandals at present are Birks. They weren't a top pick, so I am hoping they are ok in person (I've had hit-or-miss luck with Vince Camuto in the past). Fingers crossed.
Thank you again, everyone, for your feedback!