It’s hard to imagine the wife of Alexander Hamilton posing for a painting in the squalor of an 18th century prison. But while Ralph Earl’s portrait of Elizabeth Schuyler Hamilton may show her sitting in front of a set of beautiful red curtains in what must have been one of her finest gowns, the truth is that Elizabeth actually sat for Earl while he was locked up in the debtor’s prison underneath New York City Hall.

It’s an incongruous image: a scion of one of New York City’s wealthiest families and the wife of one of the Founding Fathers posing in a prison just for a painting. But as Sarah Cascone writes for artnet News, Elizabeth didn’t have much of a choice, as there were only a handful of professional artists living in the United States that could do the job.

"He was really the only trained portrait painter in the city at this time," Elizabeth Mankin Kornhauser, the Metropolitan Museum of Art’s curator of American painting and sculpture said at an event on early American portraiture earlier this month, Cascone reports.

At the time, portraits were important signifiers of wealth and social status, but there weren’t always enough artists to match the demand at hand. One painter, John Singleton Copley, spent about six months in New York in 1771, during which time he completed 37 different commissioned artworks, Cascone reports. While these works took much longer to make than a few selfies snapped on a smartphone would today, members of the upper class used their portraits to craft public personas, much like modern-day celebrities using social media platforms like Instagram and Twitter do today.

“New York’s most prominent citizens had those same concerns going back hundreds of years, and no matter how different these elegantly framed oil paintings may seem from posts on Facebook or Instagram, their inspiration remains strikingly similar,” Whitney Donhauser, director of the Museum of the City of New York (MCNY), tells Jason Shaltiel for AM New York. The museum currently features an exhibition of early American portraiture from New York City, and the museum’s collection includes Earl’s painting of Elizabeth Hamilton, as well as artist John Turnbull’s portrait of Alexander Hamilton, which was used as the basis for his appearance on the $10 bill.

When looking at portraits from this time period, tiny little details can provide all kinds of hints into who the person was, as well as how they wanted others to see them. Portraits from the pre-Revolutionary War period often let the subjects show off their wealth, capturing them dressed in their finest clothes surrounded by symbols of their social status, Cascone writes. After the war ended, however, portraits became more spartan and solemn, with the subjects preferring to highlight their patriotism over their personal wealth.

“In the mid-19th century New York City began to become modern,” MCNY curator Bruce Weber says in a blog post. “In some ways I wouldn’t say we’re that different from New Yorkers of that day. Some of their aims and aspirations were a lot like ours.”

As for Elizabeth Hamilton, dressed in a delicate white dress and the giant white wig, it appears that she wanted her portrait to communicate her elevated social status, while also maintaining some level of modesty. In the painting she wears white, with only a simple black ribbon adorning her neck and pink sash around her waist to add color. It's possible that the faint, knowing smile she wears in the painting was intended to hint at how good-humored and intelligent she was often said to be.

To check out some of these portraits in person, check out MCNY's new exhibition, Picturing Prestige, running through October 2016.