How long has it been since you hired a sitter and went out after dark? Probably too long. This is me, reminding you with a dressed up (but still comfy) outfit. If it’s a hot date, switch out the shoes for something with some height. On our (rare) summer dates, we tend to do a lot of walking – so a comfy pair of shoes is my go to. Or just go ahead and hire a sitter to run some day time errands, this isn’t a night-time exclusive uniform.