I own a dress and a pair of booties like the ones she's wearing in the first outfit, but putting them together? (thestore.com)
With this, I'd recommend short / no heels but nothing overly casual; I've found ankle booties like these go with any outfit in any season. (ordinarytraveler.com)
I would wear this one with my midi, pleated skirt and peep toe booties like shown below. (theboxqueen.com)