Thanks everyone! I've got it narrowed down (he just called to chat and confirm since he'd started making the marinara sauce from scratch!)
Sundress--would love to, but they don't look the least bit demure or casual on me.
The nominees are:
--Long black skirt (express) and strappy sage lt blue and black striped tank
--black capris and v neck sleeveless black sweater w garnet, sage and creme stripes (capris are too big on me tho)
--red capris and black ribbed sleevless polo (again, capris are too big)
--low rise jeans and a&f aqua t that laces up at the top
--reg jeans and orange plaid halter top
--low rise jeans and aqua top in first place at the moment.
And silver jewelry is a must.