The highwayman's attitude at the beginning of the poem is jaunty and confident, in line with his debonair appearance. He whistles a tune at the window and asks Bess for a kiss as soon as she appears. He then reveals one of the reasons for this good mood. He is "after a prize" which he feels confident will bring him a large haul of gold "before the morning light." This combination of certainty that he will succeed in his enterprise with his evident success in love, and the concomitant knowledge that there is a beautiful girl waiting for him at the end of his adventure, lead him to view the night's dangerous work with relish and excitement.
By the time "The Highwayman" was published in 1906, not only had real highwaymen long passed out of living memory, but the romantic archetype of the highwayman as a dashing and elegant figure was part of the popular consciousness. Much of this was due to Harrison Ainsworth's gothic romance, Rookwood, which was published in 1834 and featured Dick Turpin. The highwayman Noyes depicts is firmly in this tradition, with his dandified clothes and aristocratic manner, which set him apart from his unsuccessful rival in love, Tim, the simple ostler. In real life, the highwayman would probably have been rather similar to Tim in dress, deportment and social background.