Need opinions on HW for old medium boy

I agree it's much dressier but I've worn it casually and it looks fine too. I know personally that this bag is too small to be my everyday bag so I was okay with the dressier look. Honestly you can't go wrong with either choice. Good luck
+1

We are bag twins :biggrin:

I havent actually worn it with a "dressy" outfit yet, only casual and it looks great. The dressiest would be with a work outfit (I work in a corporate environment) and it looked just as good. Seriously can't go wrong with a Boy!