T-Roy (pronounced tee-roy) is a term used to describe white guys trying too hard to be black by dressing in outdated stereotypical black man clothes. They do this to hopefully translate the look into picking up some ladies. Especially in small towns where there aren't many brothers. Troy is the whitest name possible so that's where it originates from.
Keshawn: Holy shit dude, look at the white ass mofo over there. Rocking' his baggy ass pants, 8 inch gold rope and Timberland boots. What a T-Roy.
by Paastastic7 May 25, 2016