1. Something that is cool. Its a bit old fashioned but still in use.
2. Someone that acts in a prepotent way. Even more old fashioned, but in use. Commonly used by children in diminutive variants, "chulito" (For boys) and "chulita" (For girls)
3. Usually only in the male variant it refers to the person who protects a prostitute in exchange for a large portion of their profits.
2. No me gusta jugar con ella porque es una chulita. (I don't like to play with her because she is a prepotent)
3. Su chulo parece muy agresivo. (Her "chulo" seems so aggressive)