I want something fun, colorful, and eye catching. Nothing boring. I plan to make stickers with this logo so I want something that people will actually take the time to consider where they are going to place the sticker or they may not want hats but would actually like a sticker because it's so awesome!
I have a thought of maybe an old man's head wearing a cap. I'm open to it being a sweet looking old man , or a badass old man with possibly tattoos, piercings, smoking a cigarette.
The "Pop Caps" font could be some sort of vintage style either being above or under the logo or possibly written on the hat.
Keep in mind that where I am in Newfoundland one of our biggest industries is fishing.  So there's a possibility of incorporating fishing, sailors, boats, fog, cliffs, ocean, etc.