Fabulous dress, Shannon! Worth the struggle --- and FWIW, maybe it's your vintage accents all through last season, but the retro-ness of the shape and the floral print itself say 'Shannon' to me!
LOVE it with the black blazer and shoes in #1. Also like the idea of the pink blazer, and you have to at least try and take a photo of Angie's idea of polka-dot jacket on top (with the green shoes? *and* the oxfords too?)! I'm going against the flow here, but I suspect a low-vamp nude shoe might make it 'too sweet for Shannon' without another edgier, 'rougher' element --- which might come from a cuff or bag or moto jacket!
The blue jacket's shape is not working *all* that well, to my eye. It seems to want more length below to balance the shoulders. With pants, perhaps? Or a midi skirt in a darker colour to 'anchor' its brightness?