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Depends what your style is like! Personally I think jumbo classic flap can suit both casual and more formal dressing styles very well. Some days I even wear it with active wear, some people may frown upon that but if I love how it looks, then no one can tell me not to![]()
To me the boy is definitely more to the casual side especially for new medium size! Old medium could look more formal, but that's just my opinion
Some people may also choose classic flap over boy due to the lack of leather lining in the boy making it less "valuable", but in the end I think what matters is what YOU think matches your aesthetics.