Janelle
This hat reminds me of Hat, the Vivienne Westwood piece that Pharrell Williams sported for a while there. (I believe it lost a Fug Madness play-in game to Bag, the Birkin from Hell that Kanye decorated for Kim.) I am into the sweaterdress/tights/boots look here for SURE, and while I could not pull off a hat the size of my head, she definitely can.
And here's another version, with the same boots. When she finds a vibe, she works all the angles. I rather like this, too.
And I THINK that is the same hat as the previous slide (it's possible she's wearing the boots AGAIN here, too; I can't tell). Janelle Monae is an efficient packer. She is the living embodiment of one of those Lucky or Glamour features where they tell you how to make a week's worth of outfits from the same basic pieces. I respect that, as it is not a quality I share. However: Somehow her head is wearing more than her boobs are.