In some cases, they can't go wrong — like with the classic hat that's worn on the field. It's when they venture into some new territory that they open themselves up to a bit of criticism — and that's what they got in SB Nation's list of ugliest MLB-licensed hats.
The list includes 20 hats, and two of them are Red Sox hats. Fear not, though, as the Sox come out winners in the always-relevant battle with the Yankees, who show up on the list on three occasions.
You can browse through the gallery by clicking here, but remember: One man's trash is another man's treasure.