Galen I think one's sense of dishevelment/dowdiness etc is more in the mind than the external appearance. People who appear dowdy and untidy usually either do not know or do not care how they look.
My own DD has always been on the large size, since she was a year old, despite visits and consultations with health visitors and dieticians and my own careful monitoring of what she ate, my closest friend from school is similar. Both of them work on the basis of its not what I look like it is what I am.
DD flaunts her cleavage and as someone who swims up to 15 miles a week, winter and summer, has no hesitation about being seen in public in a swimming costume at the pool or on the beach. DF is equally gung-ho.
It is what you are, not what you look like that counts and, from your postings on GN I think your personality will outshine your figure any day.