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I can see Rae working a version of the second look.
#3 makes me think of NicoleB.
#1 is just about like that new shirt that Joy got at the rack! Joy, perhaps not with short shorts, but I could certainly see this working with bermudas or clams.
Ooh, yes, I am all over #2! My only hesitation is a long trench with bare legs - don't want to look pantless from behind. Hm, I think may have all the elements to try it out. Possibly a version of #4 as well.
Some fun ideas in there! I really love #1 (I'd totally wear that with trouser shorts) and #2. I've done heels with my short shorts in the past, but lately I am liking flatter footwear with them (not that I've gotten to wear them much this year yet!). Rae, if your trench was knee-length it would probably just make people think you were wearing a skirt