User blog comment:Videogamep/Why is Sabo Such a Big Deal?/@comment-9022101-20131213004702/@comment-972068-20131214093757

I think the man being from Roger's crew is more likely. About the hat being similar, it's a very generic looking hat. Well, not "generic" per-say, but it doesn't look unique. If there is a connection, maybe someone from Roger's crew taught someone else how to make a certain hat, so that someone else ends up making one as a gift for a certain friend, and the aforementioned crew knows about this hat because a certain member was seen with another member wearing the same hat.

But that's probably a stretch. It's not like hats have any significance to this series in any way, shape, or form.