JFK Jr. Lookalike Contest — And the Hey Hunk Winner Is…

Seven JFK Jr. wannabes, rollerblades, and preppy ’90s vibes turned Washington Square Park into a flashback—and with spring in the air, a little daydreaming was allowed.

John F. Kennedy, Jr. PHoto by Sonia Moskowitz. Flanked by two JFK Jr. Lookalike Contestants

JFK Jr photo courtesy of Sonia Moskowitz/Getty Images. Lookalike contestant photos by Jonathan Redman

Does anyone really look like John-John? On Sunday, Mar. 8th, Washington Square Park became a sea of backward caps, preppy shorts, and perfectly coiffed hair for the city’s first-ever JFK Jr. lookalike contest—a full-on 1990s throwback.

JFK Jr. Lookalike contestants. Photo by Jonathan Redman

The contest featured seven official contestants (with a few more arriving late) showing off rollerblading tricks, preppy fits, and impressive hair. Laps around the crowd, flexing, and even pushups on roller skates—these wannabes brought ’90s NYC style to life. The audience, mostly women armed with cameras and a few playful “thirsty” signs, cheered every trick, smile, and perfectly timed hair flip.

JFK Jr Lookalike Contest Winner Julian DeVincentis. Photo by Jonathan Redman

In the end, the crown (and $250 prize) went to Julian DeVincentis, 31, a Stamford native who nailed sporty JFK Jr. in a black tank, matching shorts, dark sunglasses, and rollerblades. Along with the cash, Julian also walked away with a Hey Hunk T shirt, you know, so it was official. His first words to the crowd after being named the winner? “I’m single, I’m single.” (Well, he couldn’t exactly say “I’m rich, I’m rich.” $250 doesn’t get you far these days.)

Organized by Instagram’s @heyhunk_, the contest rode the recent JFK Jr. revival sparked by FX’s Love Story, which chronicles his romance with Carolyn Bessette Kennedy. It’s debatable if anyone really comes close to looking like JFK Jr., but with spring almost in the air, a little daydreaming in Washington Square is allowed—and for a few minutes, at least, Julian made it easy to imagine.

JFK Jr lookalike contest winner Julian DeVincentis. Hey Hunk Contest 2026:
Angela LaGreca

Editor, Co-Founder/Publisher

Angela LaGreca, Editor-in-chief and co-Founder/Publisher of Spark Hamptons, is a four-time Emmy Award-winning journalist, producer, writer and comedian/host. Her TV credits include NBC’s “Today,” ABC’s “The View,” and, most recently, the primetime cable news program “Cuomo” on NewsNation. On the East End, she was the Creative Director at LTV, VP Features/Events/Photo Editor at Dan’s Papers, and has performed at Guild Hall, Bay Street Theater and the WHBPAC. Her publishing career began at Modern Photography, where she was managing editor. LaGreca lives in Manhattan and East Hampton and can be reached at angelatvmedia@gmail.com and angela@sparkhamptons.com .