Oooh what fun! Let's see here...
#1-3 are all super. I know some others found the buttoned-up jacket in #1 too stiff, but I think it makes the look. Might skew too classic for you otherwise. Totally love #2 with the flats, again adds just that little bit of funkiness. #3 works, though perhaps you might try a roll lower so the amount of skin between strap and hem is smaller; would be a bit leaner looking. I think it'll also work with flares if you can do a little heel with it. I know it's not to everyone's taste, but it's a look I'm personally fond of and sport from time to time (I managed to unearth an older photo of this, #5).
For #4, I think a lower contrast shoe might work better so that the dress is more of a stand out piece. With the high contrast footwear, it competes. I don't know that vamp would be a factor if you go low contrast, so something high or something low would work. Or, of course, the ubiquitous bootie. I do think those loafers would be really fun with shorts though (either long or short), along with a more a-line skirt to tone the girly factor of it down.
A bit torn on #5. For one, the skirt is pretty and has such cool construction! But the plain underneath side would bother me too. As far as styling, I know it would hide the wrap detail at the top, but have you tried a skirt-length fluid top? A cropped chunky sweater could also be fun.