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Bowler hat 

A bowler hat is a hat made around the mid to late 19th century in London. It has a rounded top and a curled brim. In America it is known as a "derby" due to the name of the man who made it popular, Edward Smith-Stanley, 12th Earl of Derby. The hat was very popular around 1880, but since then it's use has slowly declined. In 1960 people decided they were out of fashion, and now they are rarely seen in public. Although once in a while a tendy young upstart can still be seen sporting this retro hat as a way to look different.
Guy-1: Hey, that girl who just walked past was wearing a weird hat. I wonder what it's called.

History-slug: Why that, my good fellow, is a bowler hat.

Guy-1: HOLY SHIT A TALKING SLUG! (dies of a heart attack).

History-slug: Remember kids, always tip your hat when walking past a lady acquaintance.
Bowler hat by The History Slug March 9, 2008
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Bowler Hat 

A common name for a hair-cut that is like a bowl cut, but is parted in the center like a lane in a bowling alley. The word 'Hat' doesn't refer to an actual hat, but rather to the hair itself.
Jackson: "Wow! Look at the kid in this photo with the bowler hat."

Sneha: "Yeah, with a haircut like that the kid should pick up bowling."
Bowler Hat by bowlingluver489 March 19, 2019

bowler hat lesbian

The 1930’s equivalent of a masc lesbian
bowler hat lesbian by PissMoms November 6, 2023

Bowler Hatting 

Ramming a mega dildo or fat cock at an angle up the wrongun of a woman so that a domed prolapse appears out of her clunge. This bordered by the piss flaps gives the appearance of a bowler hat.
Last night I caught my missis with her legs thrown over the back of her neck with a rolling pin up her ass bowler hatting in front of a mirror.
Bowler Hatting by scruffystuff September 21, 2011

Bowlerbate

To slide two fingers into a womans vagina and one finger into her ass. Much like "the Shocker" but with a twist, on the verge of climax, you lift her off the ground and toss her forward, much like a bowling ball.
Example #1 -

Ken: How'd your girlfriend break her neck?

Rob: Oh, we tried bowlerbating and she flew into the wall.

Ken: Ouch...

Example #2 -

Husband: Hey Honey, would you like to bowlerbate?

Wife: Sure, just don't throw me too far this time.
Bowlerbate by Jnyxx July 12, 2010