This is a reproduction of a portrait of Sir Hugh Willoughby by an unknown artist. Willoughby was an English soldier and explorer, remembered for his voyages to find the Northeast Passage to Cathay. The painting gives us many clues about the cultural and historical context in which it was made, most notably through the visual codes of wealth and status, the clothing, for instance, marking Willoughby as a man of means. It also signifies the social conditions that shaped artistic production. How did Willoughby want to be remembered? As a man of learning? A man of action? As a leader? These are some of the questions the portrait asks. To understand this portrait better, research into the history of exploration in Tudor England would be helpful. Archival sources may reveal more about the life and legacy of Sir Hugh Willoughby, while an understanding of the Tudor court and its artistic patronage will enrich one's understanding of the image.