My boyfriend is out of town, so I get to stay up all night playing in my closet!

I'm trying to figure out whether I need some new shoes to wear with cropped/ankle pants to work this spring/summer. The black oxfords and the nude walking flats are recent purchases that can still be returned if they do not work. At first I was planning to get nude oxfords to wear with my short pants, but then when I tried them on, I wondered whether that was the best idea with a wardrobe of dark colored bottoms (the navy J. Crew ankle pants pictured and their black twins, and this pair of black crops). So instead I went with the black Nayas. I got the nude sneaker flat things on a whim simply because they are so comfortable. They don't have to be for work, but now I'm wondering whether I need those at all, since I do have my Ugg mocassins. I also have black, cognac, and coral pumps that live at the office (not pictured).

Ok, so my questions:

-Which shoes look best/worst with the ankle pants? Any better ideas?
-How is the length? I am somewhat considering letting the hem down on the black ankle pants (not shown) and taking it up on the navy ankle pants.
-Which shoes look best with the dress?
-Do any of these shoes need to be let go? Do the new ones add something to my shoe wardrobe?

*Bonus pic of my shoe guardian! Thanks for looking!

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