Hi Firecracker --
I'm duplicating remarks above but I don't care!
First, the jacket from Chez Firecracker is stunning in and of itself (the fabric mix and detailing) but more importantly amazing on you in terms of color and shape. Did you use something like Claire Shaeffer's couture sewing techniques for the construction? Cause it sure looks fancypants.
Onto your sale picks.
The grey blouse is beautiful on you and makes your face glow, (ditto for the wine, which I agree is different enough from the sleeveless you aren't wearing much due to its sleeveless nature). I hear you on the $$$ for the grey, though; I ended up with a sale Vince in Feb/March but only kept it went it went down again. However, I'm not a big blouse person except in warmer months and it seems like you are, so.... /enabler-Cost Per Wear analysis
The green, the scarf, the camo blouse -- you really know what suits you!
[I do echo Marley re the coated leggings, though; if wearing them with shorter blouses (as pants) vs tunics (as leggings) I'd try sizing up.]
Re the aging hobo -- have you taken it to a shoe repair place in addition to DIYing with leather conditioner? I find my techniques only get me so far; while I like the new bag, if you're on the fence about replacing and/or not having the hobo in rotation, think taking it to the pros and seeing what they can do.