Green’s Dictionary of Slang

chester n.

[? Chester (the) Molester n.]

1. (US Und.) a second-rate criminal.

[US]Monteleone Criminal Sl. (rev. edn).

2. (US campus) a socially inept person.

[US]Eble Campus Sl. Fall.
[US]Eble Sl. and Sociability 94: Chester, for ‘someone who is cheezy (socially unacceptable or unfashionable)’ comes from a cartoon character in a Cheetos commercial who keeps saying cheezin’.