Green’s Dictionary of Slang

1. (US black) a Rolex watch.

2012		Chief Keef ‘Kobe’ 🎵 I say baby I got the racks she like you need to show me / [...] / On my right wrist Versace on my left wrist a Rolly.
2020		G. Krauze Who They Was 12: He starts showing me on his Rolly how I have to grab the watch face and jerk it at an angle.

2. (N.Z. prison) Rolleston Men’s Prison, Canterbury.

2001

D. Looser Boobslang [U. Canterbury D.Phil. thesis] 155/2: Rolly n. Rolleston Men’s Prison, Canterbury.