A man wearing glasses and a ragged costume is playing a Jaguar electric guitar and singing with the accompaniment of a drummer.
A man with glasses and a disheveled outfit is playing a guitar and singing along with a drummer.
Ragged means dishelved and the rest sentence is same
With glasses and wearing glasses both imply that they have glasses on their face.  A ragged costume and a disheveled outfit both imply  that the clothes someone is wearing are old and/or sloppy unkept.  A Jaguar electric guitar is a type of guitar.
Man wearing glasses is a paraphrase of man with glasses, and ragged costume implies disheveled outfit.