I love all the pieces on you, but I'm not sure I like them together.
This may just be me -- I haven't been able to get the bootie/skirt look to work yet. The booties are adorable and I'd wear those to death with slacks. For skirts, I'm just not crazy about how high on the ankle they are hitting you. I think it may be more leg lengthening to have a bootie that hits lower? Then again I may be overly picky about such things, since my legs are short.
You are looking for bold color -- what about adding it in the top rather than the jacket? You are wearing a lot of black and I'm wanting to see you in a top that's not black with these skirts. Orange or cobalt would work, white would also work. Or a denim shirt since you want to make it less corporate and more casual.
What happens when you tuck the tops into the skirts? I'd like to see the tops hit a bit higher (where the jacket is hitting on your hip), or tucked in. If that's too "va-voom" for casual night out, try a boyfriend length sweater?
If I was going for casual, funky night out, I'd wear the RR skirt with knee-high, flat black boots. Flats to me tend to read casual. I'd layer black micro-fishnets over cobalt blue tights if I was feeling especially funky: the layering gives it a subtle effect. Then I'd wear a denim shirt tucked in at the waist, with a gray boyfriend sweater layered over it. Or perhaps I'd go with a simple, basic white cotton tee tucked in with a jean jacket over it. Somehow I'd bring denim into the look since it is the quickest way to read "casual." I'd then bring a splash of color in with a purse, in orange or cobalt.
Or maybe I'd find a cozy oversized sweater in a bright splash of color and partially tuck it in the front -- or not. Go for the slouchy on top look, svelte on bottom. The leather jacket might then work because you'd have the contrast of textures. Cozy sweater with leather.
You do not have to wear a black top with these skirts -- that's what makes them so versatile. You don't need to wear a white top either. A soft grey would work. Any bold color would work too. You could also wear it with the beiges that are so in style right now, if those work for you.
Just some brain storming for you -- I think you have chosen excellent, versatile pieces. I wouldn't give up on any of them yet. I would love to see that orange jacket paired with plaid wool drapey slacks in shades of brown. That could be interesting! Do you wear earth tones? That orange could really liven up an earth tone outfit. Now that I think of it, if you do wear earth tones, then the orange may prove to be far more versatile than the cobalt. There's so much beige in the stores right now. I would love to see the orange leather jacket paired somewhere with leopard print *something.*