When you are engaged in sex and the man is wearing a fitted hat, he removes the hat, ejaculates in the hat, then places it on the ladies head.
I Came in Dis hat then put it on her head...Now she got "The Fitted Hat"
by J Babes October 24, 2008
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A hat(or cap) with an almost completely flat brim. Popular brands are "New Era" and "59FIFTY". They are not adjustable (hence the fitted) and usually come with gold stickers. The hat loses value if you remove the sticker. Prices range from $20-$50. Popular with gangstas.
Don't you think that fitted hat is G?
by CoolLarkin November 2, 2008
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The crown for douschebags. People who wear these hats usually exhibit most or all of the following traits: Thinking they are actually cool, Talking down to random strangers, Talking sarcastically to authority figures because it like the hat makes them feel 'badass', Live with 1 or less testicles, Like to pretend like they can skateboard, Think wearing this fitted hat gives them permission to talk to women like they actually have a chance, Think they are above common courtesy like taking off that hat indoors or even opening doors for women or anyone for that matter. These hats usually have no actual effect at blocking out sunlight because wearers usually tip them so far up.

*Note All Above Rules DONOT Apply If The Wearer Is Black*
"Haha dude look at that poser over there trying to skateboard, he just faceplanted and lost his fitted hat."

"Kid, back off my girlfriend and its not even sunny outside so take off the pointless hat.
by ono412 September 15, 2010
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white sox hat... something you do NOT wear to homecoming.
Im wearing some cakeys with my fitted hat to homecoming tomorrow.
by LAAUNRDERNEA October 13, 2007
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