If I had a dress like this (and believe me, I've been fantasizing about it for awhile!), I imagine I'd pop a collared blouse under it. I don't know if my taste is wonky or what, but I might even try a denim shirt under it. That might work, tonally, with those booties?
As for tights and shoes, I'm confused because I thought in Angie's blog post about WTW with leather skirt, the advice was to wear bare legs or nude fishnets or sheers, with pumps? Not with tall boots (too much leather?). Also pairing suede footwear seems to be a good strategy since it adds texture? What am I missing here? Is it because this shift is shorter than a pencil skirt it needs a different approach?
As for topper, I have experimented around with my leather skirt (not a shift dress, sigh... ) and what seems to work best is a 3/4 length coat. Like a wool coat. Or, I have this statement gold brocade 3/4 length topper, shown below.... may be too lady like for what you're going for.... but the idea is to add a contrasting texture and pattern.
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