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We are grateful to Jacqui Ansell, Senior Lecturer Christie’s Education, for her commentary on men’s fashion which has been incorporated into this catalogue note.


Exploration during the Elizabethan age was pursued only by the most skilful and daring men at court. It required bravery, intelligence, and the ability to lead and command – a set of skills perceived by contemporary courtiers as profoundly masculine. Their exploits, most notably piracy, reaped great rewards for both themselves and the crown and their successes were celebrated in literature and art. This portrait was most likely commissioned to commemorate a foreign expedition and fuses a visual narrative seldom seen in portraiture of this scale from this date, with a conspicuous, if slightly fantastical, display of status and wealth through dress.

The sitter in this portrait is most likely Sir Robert Dudley, the illegitimate son of Robert Dudley, Earl of Leicester, who led an expedition to the West Indies in 1594 – the...



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We are grateful to Jacqui Ansell, Senior Lecturer Christie’s Education, for her commentary on men’s fashion which has been incorporated into this catalogue note.


Exploration during the Elizabethan age was pursued only by the most skilful and daring men at court. It required bravery, intelligence, and the ability to lead and command – a set of skills perceived by contemporary courtiers as profoundly masculine. Their exploits, most notably piracy, reaped great rewards for both themselves and the crown and their successes were celebrated in literature and art. This portrait was most likely commissioned to commemorate a foreign expedition and fuses a visual narrative seldom seen in portraiture of this scale from this date, with a conspicuous, if slightly fantastical, display of status and wealth through dress.

The sitter in this portrait is most likely Sir Robert Dudley, the illegitimate son of Robert Dudley, Earl of Leicester, who led an expedition to the West Indies in 1594 – the same date inscribed beneath a rock in the lower right. The portrait probably commemorates his discovery of Dudleiana, an island in the Caribbean that he claimed for the English crown in 1595. Various aspects of the portrait inform the viewer of Dudley’s struggle in his noble ambition to command and conquer. In the background we see a ship flying a naval ensign with a St George’s Cross flag on the main mast, and to the right we see the ship’s tender rowing sailors to the shoreline. A tree wrapped in ivy, symbolic of strength and immortality, is visible on the right, from which hangs a shield inscribed with the Latin motto 'non reiecienda reiecta' (‘that which has been rejected should not have been rejected'). This is perhaps a reference to the Queen’s rejection of Dudley’s initial request to circumnavigate the globe; he was deemed too inexperienced but was granted permission to sail to the West Indies instead. Shown here standing on a conquered island, Dudley is proving his critics wrong.

The style of dress seen here broadly corresponds with court fashion from the 1590s which emphasised a strong, linear silhouette achieved here through a long body, tight sleeves, pronounced shoulder wings and a tall hat. Other aspects of the outfit, however, are less easy to pin-down and it may be the case that the artist, who is at present unknown, modified the outfit in order to prioritise opulence over accuracy. The gold embroidered doublet, for example, is of an unusual construction and has a profusion of pockets not seen in daily dress. The shoes and stockings are further anomalies and bear little resemblance to those worn in European circles at this date. However, the fashionable combination of a fold-down collar and small, neat ruff worn at the neck demonstrates an acute awareness of the latest fashions in England and reminds us that portraiture at this date was sometimes a careful balance between fact and fiction.

Dudley’s impressive outfit is accompanied by various accoutrements of war. In his right hand he holds a halberd, a popular weapon that consisted of an axe blade and sharp spike mounted on the end of a spear, and around his waist he wears a sword with an oriental-style handle. At the base of a tree to his left we see a shield and helmet embossed with pagan imagery in a manner reminiscent of armour used in tournaments at this date. These accessories infer defiance, a seriousness of purpose and a willingness to fight for a cause – all attributes associated with contemporary concepts of male power.

The life and iconography of Sir Robert Dudley

Although lacking experience, Dudley, who had evidently inherited his father’s confidence, recruited 275 sailors and set sail to the West Indies on 6 November 1594. Although his initial attempt was scuppered by a storm, his second departure was more successful, and by December he was in Tenerife where he succeeded in capturing two Spanish ships which he renamed Intent and Regard. Dudley’s fleet then sailed to Trinidad and anchored at Cedros Bay at the end of January 1595. It was there that he discovered an island which he named Dudleiana and claimed for the English crown. Following a failed attempt to find gold, the fleet sailed north where it captured a Spanish merchant vessel, however, with provisions dwindling, further progression was limited and Dudley decided to sail home, arriving in St Ives, Cornwall at the end of May 1595.

Following an expedition to Cadiz the following year with Robert Devereux, 2nd Earl of Essex, Dudley was knighted. Soon after, he married Alice Leigh, daughter of Thomas Leigh of Stoneleigh, although the union was not to last and following a failed attempt to claim his late father’s peerages, he fled England with his cousin Elizabeth Southwell and the pair were later married in Lyon after converting to Catholicism. They then travelled to Florence where Dudley became a naval advisor to Ferdinand I, Grand Duke of Tuscany. In 1607, on refusing to travel back to England on the orders of James I, Dudley’s lands were confiscated although he maintained contact with the English court through a network of friends.

In his later years, Dudley published Dell'Arcano del Mare (‘The Secret of the Sea’), an impressive six-volume maritime encyclopaedia which included an atlas of the entire world. It was published in 1646-7 and covered topics including shipbuilding, navigation, and astronomy. Dudley died soon after in 1649 and his collection of scientific instruments are now on display in the Museo Galileo, Florence.

Dudley’s iconography is sparse, and his best-known portrait is that by Nicholas Hilliard in the National Museum of Fine Arts, Sweden, painted in the 1590s. Although painted in a different medium, Hilliard’s likeness of Dudley bears a striking resemblance to the subject in our work, which was probably painted sometime after his return to England in 1595 and before he left England for Italy in 1605.

This portrait was sold by George Sutherland-Leveson-Gower, 5th Duke of Sutherland in 1924. According to an inscription on the reverse of the canvas, it was previously at Trentham Hall, Stoke-on-Trent, and was then brought – presumably to London – to be cleaned in 1850. Trentham was inherited in 1605 by Sir Richard Leveson, who married Katherine, daughter Dudley and his first wife Alice. If was presumably through Katherine that the present work found its way into the collection of the Dukes of Sutherland, who also owned a full-length portrait of Robert Dudley, Earl of Leicester, by Federico Zuccaro, which is thought to have been destroyed during the Second World War.

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500 Years of British Art