Keep the dress and the dark wash shorts.
I have a Loft black cotton tank-top pullover dress that is a workhorse. I've topped it with a white Jean jacket, a blue jean jacket, the embroidered Zara bomber jacket. It's been to work, to dinner, to the Caribean, and to a funeral. You can style it with flip flops, sneaks, or heels. It's a no brainer basic.
The dark wash shorts just plain look great on you.
I have a poison eye for cameo. Sorry! Just not a fan of the print.