i like that haircut, i think it should work for you. (i would not think of it as a pixie). i would wear that style curly, not straight. (btw, while boston is not as humid as florida, it can be pretty humid in summer). i also have a round face and i've been told by stylists that i should not have my hair cut to my cheeks, but cut either above or below. so chin length is good. i have between chin and shoulder length.

what specific products are you using? mousse can dry out your hair.
and, how is your hair cut, are there layers? short or long, you need some long layers for curly/wavy hair, otherwise we get the triangle effect .
key word being LONG layers, not chopped short on top!!

i think you should try to get your hair as healthy as possible and if you wear that cut curly/wavy i think you will be happy with it.
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3a, some 2c & 3b, medium texture, porosity normal, low elasticity
washing/cowashing, conditioning, protein tx: curl junkie products
leave in:cj conditioners and treatments as leave in
styling: cj pattern pusha, cj honey butta leave in, cj cccc, cj ciab, lalsg. cj aloe fix gel is my high dews/summer HG!!
sealants - spiral solutions emollience butter, jane carter nourish & shine