He was visorless at least twice in the films: in the climax of the first film, when Magneto took his visor to force him to keep his eyes closed, and in The Last Stand when Phoenix was holding back his eyebeams.
Those were isolated incidents and only two times in three films. You're also forgetting the mid-section of the first film when Toad used his tongue to whip Cyclops' visor off, FWIW. So technically three times. My point being, though, that Cyclops either had glasses or a visor on during most of the time he was on-screen, so I don't see the problem with Judge Dredd never taking off his helmet.