Checkered shirts are a stereotype of the male pop generation. The are fashionable which also advertises effectively and influences the younger audience to also purchase them. Bruno Mars is a well known singer who we see in almost every music video wearing one.
Leather Jasckets are also a popular element in music videos surrounding the pop genre and related genres such as indie or rock.
Converse trainers are beyond the most popular brand of trainers in the world, they are worn by hundreds of singers in music video, they are seen in Rock, Pop, Indie, Metal, Emo etc genres.