I struggle with making predictions about whether I'll like something years from now - statement pieces and simple basics, alike.
I would recommend going a size up on this top - my usual size was way too small in the neck!
Jeans: Gap, $32 (similar, similar, similar)
Shorts: Gap, $20 (similar, similar, similar)
Heels: Jessica Simpson c/o, $59 (same)
Flats: Sole Society c
Macy's, $130 (similar, similar, similar)
Earrings: My Stella & Dot
Approx.