Boyfriend and Girlfriend Donald Trump with Melania Knauss in 1999

Back in 1999, a famous photographer named Patrick Demarchelier took a bold and eye-catching photo in New York City. The stars of the photo were Donald Trump, who was then a well-known businessman and property mogul, and his girlfriend at the time, Melania Knauss, a 26-year-old Slovenian supermodel. The two had met just a year earlier in 1998 at a New York Fashion Week party and were now a high-profile couple.

The photo was part of a shoot for British GQ magazine, which published it in January 2000. At the time, Trump was dabbling in politics, trying to win the Reform Party nomination for president, and he loved showing off his lavish lifestyle—like his custom Boeing 727 jet, where part of the shoot took place. In this particular image, Melania is posing on a desk, wearing a star-spangled outfit with American flag boots, while Trump sits behind her, talking on a phone. The scene is dramatic and patriotic, with an American flag in the background, capturing the over-the-top vibe of the late '90s "lads mag" era—think flashy, provocative, and unapologetic.