If it were mostly black with orange, I think the Halloween connection might be a problem. But if the top underneath is white, I think you will have enough lightness to avoid looking like you are waiting in the pumpkin patch for the Great Pumpkin. The halloween association also varies according to the shade of orange. A more citrusy color looks springy or summery. A darker orange looks more autumnish.
Essentially, I think the longer, fuller skirt with the feminine shoes reads as 50's retro to me, which is a look I really like. A shorter cardi and top would fit into that theme, and would work better with the shape of the skirt. Another possibility I thought of would be a button up blouse, hitting no longer than mid hip, with some waist definition. You could pick any color, but I think brights would look the freshest.
The black shoes work in my opinion, but they look safe. A shoe that matches or coordinates with the color you wear on top would freshen up the outfit. If you don't have shoes that will work, consider matching toenail polish to the orange cardi, or whatever color you choose to wear on top. I find that a fun or funky pedicure makes even the most conservative outfit more fun.
I would love to see how the orange cardigan works out.