In this portrait, Boylston wears a ruffled undershirt, while a damask banyan cascades in regal folds around him, and a velvet cap sits atop his shaved head. Copley prominently displays the source of Boylston’s wealth: there is a shipping vessel, or brigantine, floating in the harbor behind him, while Boylston’s left arm rests protectively on two account books.
Boylston’s firm would have advertised its imported goods in local newspapers, the way Mrs. Ann Graham does in this advertisement. Boylston’s damask and velvet would have been British imports as well; there were several 18th century policies that forbid the manufacture of “wool, linen, silk, and cotton cloth” in the colonies – Britain was highly protective of its own industry, and wanted to benefit from the demand for fine fabrics from wealthy colonists like Boylston by forcing them to import directly from them. These fabrics would have either been smuggled in to the colonies or highly taxed, and would have come at a high price.
1769 marked a time of increasing revolutionary thought in Boston. Though Boylston's politics are not apparent in this portrait, the portrayal of such lavish imported fabrics, as well as a ship in the background, at a time when the non-importation debate was raging seems to indicate which side Boylston would ultimately choose – that of continued importation of British goods, and business as usual. Like Copley’s father-in-law Clarke, his decision was met with rage from members of the Boston public who supported non-importation. In 1771, two years after this portrait was painted, a ship similar to the one portrayed in the background, owned by Boylston’s firm, was seized as it entered Boston harbor and its British goods confiscated.
The banyan Boylston wears here was meant to be casual, indoor wear, and was heavily influenced by a vogue in Asian-inspired styles that had gone into vogue in Europe during the 18th century. Boylston wearing such a garment would indicate that he not only enjoyed leisure time but could afford to purchase fashionable yet fairly nonfunctional garments.
Boylston used his wealth to adorn his body and home with luxurious textiles, and these efforts did not go unnoticed. John Adams, upon visiting his elegant mansion on School Street, described the home in his diary, and focused primarily on the richness of the fabrics as evidence of his high status: “A seat it is for a nobleman, a prince. The Turkey Carpets, the painted Hangings, the Marble Tables, the Rich beds with crimson Damask Curtins and Counterpins, the beautiful Chimny clock, the Spacious Garden, are most magnificent of any Thing I have ever seen".
These fabrics both allowed him to both flaunt his wealth and acted as a sound investment after his death – although it is not clear if Boylston actually owned the damask banyan in the painting, he evidently had enough sumptuous clothing that he saw it fit to leave his collection of “Wareing Apearelle” to his brother Thomas II in his will.
Boylston being depicted glossy silk and fanciful print is particularly striking when one considers that men's clothing was moving towards the “very confining and very much non-draped....” The clothing of wealthy men, as shown in this portrait of Mr. Goldthwait, was taking on more somber, neutral tones, with drapery, flashy prints and flamboyant colors increasingly relegated to women. Copley undercuts this trend by presenting Boylston in casual clothing instead, giving him an opportunity to display his skill in presenting dramatic swaths of drapery.
However, as colorful as Boylston’s attire may seem, particularly in comparison to more formal portraits of his male colleagues, Copley appears to be following the shift towards somber male attire and a focus away from male clothing as an indicator of wealth in the Boylston portrait as well. Though still fanciful and flamboyant, the colors of the portrait have been toned down considerably. In an earlier version of the portrait, painted in 1767, his clothing is identical, but of a brighter, more teal hue. In the 1769 portrait, the darker banyan, as well as a dulling quality to the sheen of Boylston's clothing, put the focus of the painting further on Boylston as a person, adding a greater sense of personality and humanism to the man. This change has the overall effect of portraying "the Boston merchant as a man of powerful presence and distinction as well as a man of lavish tastes". The improved portrait, with its sumptuous yet restrained fabric in favor of a focus on Boylston's face, may indicate that Boylston wished to be viewed as an ostentatious and charismatic man, yet a dynamic and serious merchant as well.