Transformed from clean cut to scruffy in his mug shot, Shia LaBeouf attempts a smile after his arrest in Chicago early Sunday morning.

The booking shot, posted on The Smoking Gun, was a first for the Transformers star. The 21-year-old actor was busted for misdemeanor trespassing in a Walgreens around 2:30 a.m. after he was repeatedly asked to leave the store because he appeared intoxicated, police said.

He is due in court Nov. 28 in Chicago.