Hidden Jeans Cotton-Blend Shirtdress Dress - I hemmed mine (myself, ooops), so while I lost some of the fun distressed elements, it fits better on a 5'3 human. The distressed elements will come back with wear and washing, too.
Gucci Backless Loafers - yes, they're so "trendy" right now, but these are also comfortable and classic, a happy medium between "trendy" and perennial, formal and laid-back. I wear mine everywhere - and no, they haven't creased, like I've heard women express concern for.
Celine Shades (on sale here!!)