Spending a girlfriends' weekend in Chicago -- all 60-plus retirees. No idea what to wear. Just casual. Can I wear my black cotton cropped wide leg pants (Target A New Day - 2 years old! ...or is it 3? :0 )? If so, how do I layer them for the windy city and unpredictable weather mid May?

I'm willing to buy a few pieces to layer, but I don't know WHAT. Short denim jacket? Something else? For Saturday, we will be touring, going to early dinner and SC show.

Also, can I wear my white cross trainers? (I have AWFUL feet.) TIA!