18 Important Moments in Backwards Kangol History

The popularity of the debut season of Ryan Murphy’s Love Story—a limited series on the tumultuous, stylish, and very public lives of John F. Kennedy Jr. (played by Paul Anthony Kelly) and Carolyn Bessette (Sarah Pidgeon)—ignited a nostalgia-fueled obsession with the couple’s style. On her end, Bessette was a publicist for Calvin Klein in the ’90s; her closet, like Klein’s output around the same time, skewed minimal—the timelessness of which makes it a rather seamless look to replicate today. But JFK Jr.’s presentation was a bit more sprezzy, much of it owing to his charmingly wayward nature.

For example, John-John would often bike to work in a suit, lock the chain around his waist, and seemingly forget the key at home, leaving him in the position of taking meetings with a heavy-duty belt hanging off his body. On these bike rides, he also displayed his elite taste in headwear—namely, the backwards flat cap, a niche classic. Though Kennedy’s contribution to the form was notable, the flipped Kangol predated the political heir; Run-DMC owned Kangols in the ’80s, the maneuver featured heavily in the 1991 cult classic New Jack City, and the caps went on to see a colorful life in this millennium, too.

In celebration of the new generation of JFK Jr. style appreciators, we rounded up some of the best backwards-Kangol celebrity moments. From the king of the Kangol, Samuel L. Jackson, to the red fleece berets that Team Canada wore to the 1998 Nagano Olympics, here are some of flipped flat cap’s greatest moments.