The operator of a motorcycle: Question The operator of a motorcycle: Answers Must wear a helmet if under the age of 18. Must wear a helmet if they have held their license for less than two years. Should not wear a helmet. Is safest when not wearing a helmet. Explanation In Hawaii, any motorcycle operator or passenger under the age of 18 must wear an approved helmet while riding. It is recommended that all operators and passengers wear helmets while riding motorcycles.