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John Smart painted the British gentleman Constantine Phipps (1746–1797) at the age of twenty-four, executing this portrait in 1770, the year following the death of the sitter’s father, Constantine Phipps (1710?–1769), and preceding his marriage to Elizabeth Tierney (d. 1832). Phipps the younger was the second son of a landowner and lived throughout England and France. In 1788 he moved his family to Caen, Normandy, hoping to educate his ten (eventually thirteen) children more economically. Phipps and his wife returned to England in 1792 to attend their daughter’s wedding. The escalating conflict between France and England prevented Phipps from returning to France where he had left eight children behind. Unfortunately, he did not see them before his death five years later. <br>The portrait represents Phipps’s nearly full face. He has light brown eyes and natural brown hair worn <em>en queue</em>. He wears a green coat with a small collar, a white waistcoat embroidered with gold, and a high, white stock collar. Phipps is depicted against an olive-gray background. This early work by Smart already exhibits hallmarks of the artist’s style, such as the plain, gray background, the sitter’s colorful clothing, and his expressive eyes and slightly upturned mouth, which suggest that Phipps was a self-assured man with a sense of humor. The small format is also characteristic of the first decade of Smart’s career. <br>This miniature is mounted in an elaborately carved gold frame on a bracelet made of gold and woven light brown human hair. The bracelet was executed later than the miniature and is in the style of the 1830s or 1840s. The inscription on the clasp reads “E. C. E. T. / Nov.r 29th 1838, aged 7” and may indicate that this bracelet was given to Constantine’s great-granddaughter Elizabeth Clarissa Emilie Toker (1831–1888) on her seventh birthday possibly by her mother or grandmother. <br>There is a variant of this work in the Phipps collection in London. Painted in 1771, this miniature descended from Colonel Pownoll Phipps, the seventh child of Constantine Phipps, to John Constantine Phipps.