Enrique got his hands on a brassiere as he performed an intimate gig at Terminal 5 in New York.
The 38-year-old singer was spotted pressing the padded bra to see if they fitted his manboobs, the Sun reported.
Later, the Spanish star got the lingerie off his chest as he took a peep inside the cups.
After finding the cups empty, Enrique, who was apparently having fun with the apparel, did his best to look shocked and tossed the nude-coloured undies around his neck.