I tried some different combinations with my new leggings today. I'm afraid the color on the dress and the leggings doesn't come out well in the photos. I think they go well enough together (photos 1 and 2)--same color family, one lighter than the other and different textures. I tried a few different jackets (3, 4, and 5)--I'm not sure if toppers work differently with the monochrome version than they do with black tights/leggings.

And then there's the black-on-grey print leggings (detail in photo 6). I'm planning on wearing them with my black and my grey sweater dresses, but I thought they might work with this skirt and its faux-slip detail, even though it may get a little busy: 7 through 11. Too much? Multiple photos of the cropped jacket, which I decided to wear simply because it was the last thing I had on and time was running short. I'm not entirely sure about the grey-on-grey, but I thought I could get away with it because of the different textures. And then I throw on the red scarf whenever I worry that an outfit with all neutrals is looking too drab.

Edited to add: I'd also appreciate footwear comments. I simplified by just wearing what I thought was a good enough pair with each of the two sets of outfits, but I can easily see black knee-high flat boots with the plum/burgundy dress. (Or oxfords.) I felt the longer A-line skirt called for heels rather than flats. (I love my oxfords, but with that skirt I suspect they'd be too schoolgirlish.) Am I on track?