Rembrandt shared Hals's commitment to psychologically penetrating portraiture in the Dutch Golden Age, using warm tones and expressive brushwork to animate individual sitters with remarkable personality and inner life. His self portraits and commissioned works achieve the same sense of direct human engagement and Baroque vitality seen in The Laughing Cavalier.

Van Dyck produced aristocratic Baroque oil portraits of similarly elegantly dressed sitters with rich costume detail and commanding presence, working in the same 17th century Northern European tradition of expressive figurative realism. His ability to convey status and personality through pose and painterly technique closely mirrors the qualities that define The Laughing Cavalier.

Verspronck was a direct contemporary of Hals working in Haarlem who produced Dutch Golden Age portraits with similar compositional framing, warm oil paint handling, and attention to the sitter's individual character and costume. His bust length portraits of confident, well dressed subjects share the intimate yet vibrant spirit of The Laughing Cavalier most closely among Hals's peers.