Saggy Knit Cap (hipster hat)

[BoomerD]

http://www.etymonline.com/index.php?term=toboggan



That kinda makes sense, although during my search I see its mainly people from the south that call the hat a toboggan.

https://en.wikipedia.org/wiki/Knit_cap

Other names for a knit cap include: sock hat, knit hat, knit cap, "bonnet", sock cap, stocking cap, tossel cap, ski hat, toboggan (Southern American English), burglar beanie, watch cap (American English), woolly hat, snookie, sugan, or chook.
In parts of the English-speaking world, this type of knitted hat is traditionally called a "beanie" rather than the less popular "knit cap". In parts of Canada and the US, the word "beanie" is used to denote a completely different less floppy cap that is not knitted, but rather made up of joined panels of felt, twill or other tightly woven cloth (see Beanie (seamed cap)).
The knit cap is also known in Canadian English: tuque (pronounced /ˈtuːk/; also spelled touque or toque in Canadian English), a word closely related to the French word toque, originally referring to a traditional headwear and now used for type of chef's hat (short for toque blanche, meaning "white hat").
A knit cap is commonly referred to as a "watch cap" by members of the United States military, as it is the head gear worn while "standing watch" on a ship or guard post.
A knit cap with ear flaps is often called a bobble hat, toboggan, or sherpa.

 

[olds]

I call them ball sacks.

 

[Childs]

https://en.wikipedia.org/wiki/Knit_cap

Right, if you aren't from the south or never spent time there you would probably think of the sled, not the hat.