This is Squiddly plush in a number of different hats.
Squiddly belongs to Forbic
Top left: Pith helmet
top middle: trilby with feathers
Top right: a white hat found in a sale
middle left: A small top hat (the two tiny top hats and the two full sized top hats did not fit but this one was just right)
Middle: A close up of his feet
middle right: a paperboy hat
bottom left: paperboy hat and goggles (thats so cute)
Middle bottom: wide brimmed black hat
Bottom right: Steampunk goggles, not useful for looking through but great when perched on top of my bowler hat

By the way, these are not all my hats. I have loads more but those not featured did not fit or suit the plush