Love the outfit with khaki blazer. Tiny people in grown up clothes is my favorite thing ever.
Red shoes. But that's my answer to any shoe question..sooo...
I'd bring the boots--we have two inches on the ground where I am (northwest of the city) more projected for today, so if the boots are to avoid wet feet....yeah, even (especially) if it's warmer by the weekend, bring 'em.
Red and I'm also in N IL, and I'd bring the boots. My boys have worn theirs everyday this week. Slushy and icy in parking lots. Not 100% about downtown.
Re: Quick vote, and Chicago question
Nancy James 9.1.12
Calvin Donald 8.27.14
Big Kid Jan 2010
Littlest Man Sept 2012
He wore his suede shoes playing in the snow, lol. Oh well. He had a blast.