Opinions please!

Gracie

So my birthday is this weekend and my fiancé is taking me to Chicago for dinner and a night out. I'm from a small town and have never dressed up for an elegant dinner or a club. Im having a very hard time finding an outfit I feel like I'd fit in with. I know this sounds stupid but what exactly do city girls wear for a night out? I have this picked out right now, Would this be acceptable? I don't want to look stupid or anything 😰