Let's start with the 8 Ball Vest. Wearing a giant 8 ball over your chest isn't going to be easy to pull off.
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Of course you need to wear some white under that for the rest of the chest area.
From there it's pretty open as long as the colors are as gray or monochrome as possible.
My best recommendation is for the shirt worn under the vest to be light, not baggy, and stretch below the waist (If the shirt can't stretch below the waist, a skirt of the same color should go under or over the shirt).
Long dress pants or faded black jeans also recommended.
Shoe's can be anything from loafers to heeled boots, but sandals should probably be avoided
In fact, that outfit in the above pictures a pretty good example all over. Still, here's more specific sketch.
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