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1.
An individual at your place of employment who is given a position of high standing, but is completely undeserving for reasons of incompetence, ineffectiveness, or a broad ignorance of subjects that are at the core of his/her responsibilities. A highpocket is someone who has the aforementioned traits, and wears his/her pants up high in a display of smug self-satisfaction. Sometimes suspendors or a tight belt produces this effect. A highpocket is generally despised by those who perform actual work, since a highpockets tends to do tedious, unimportant work and thoroughly laud themselves for what they believe to an outsanding contribution.
Employee 1: Have you met the new marketing director?
Employee 2: No, is he cool?
Employee 3: Hell no, the guy sits in his office all day making tps reports. What a fucking highpocket.
by BernieMadoff February 25, 2010
 
2.
A tall individual.
Hey, highpockets! Can you get this kite out of this tree?
by tradesman May 07, 2003
 
3.
Someone who is really cheap, and therefore can't seem to reach into his pockets. Also known as having short arms.
Did you ever notice that Steve never takes his turn picking up the check? Let's start calling him Stevie High Pockets!
by HotJewLover June 28, 2011
 
4.
An old 1960's-era slur on the previous generation of men who grew up in the 40's, who commonly wore extremely high-waisted pants with the waistband pulled up above the navel.
"Hey, check out 'highpockets' over there. Any higher and his pants would be up under his armpits."
by Lord Percy Fondlebottom July 23, 2014
 
5.
Noun - Having a very large, very high ass. Refers to the placement of the pockets on pants in relation to the neck.
High pokets there puts his wallet in his pants over his shoulder.
by Saliari March 07, 2005