Chickadee is precious! You are so lucky to have those wonderful, pretty slings- the slings available when mine were little were very baby blanket-ish, not a good look, but we didn't really care because there were no other options.
I think the dress and leggings look is perfect on you. You look so effortlessly put-together. I love the teal and yellow cardigan and the purple. I wonder if the gray would look best with a black cami- just to balance all the black length below.
Congratulations on finding such a great and easy look to wear for MOTG. And it'll still work next year when you're chasing adorable Chickadee around the playground.