gumboot oliver 

A guy who wears inappropriate footwear to nightclubs in a vain attempt to be noticed. In other words a characterless loser, grasping at anything that will set him apart from the crowd.

A sslf absorbed, unaware twat, who is laughed at in pity.

Person 1:"Look at that guy, hes got plastic bags for shoes."

Person 2:" SOOO Lame, he has small genitals, what a gumboot oliver!!"

gumboot oliver by smoka36 March 13, 2010