#1 outfit is what I wore yesterday and was very happy with the colour combo. Unfortunately, the fit of pants in the crotch area is too tight to wear with a semi tucked top without a jacket.
For #2, I am not sure about the proportions. To your eye, does the first one look better or the second one where I have rolled up the Bf's one more time? I didn't realize it earlier but looking at these pics, I think this look is extremely leg shortening.
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