JFK Jr. Lookalike Contest: A Fun Showcase of Charming Men in Hats
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At the John F. Kennedy Jr. Lookalike Contest held in Washington Square Park, a diverse array of participants embraced the spirit of the event. Beneath the park’s iconic arch, a sporty lookalike donned short shorts and New Balance sneakers for a photo. Nearby, another contestant, wearing a quirky vest and sporting drawn-on chest hair, added a humorous flair. The contest’s victor, a tall competitor on roller skates, attracted attention from nearby singles and curious onlookers.
This event, inspired by a series of viral flyers, called on Manhattan’s handsome residents to demonstrate their city pride. Participants were encouraged to sport their best ’90s outfits as they gathered on March 8 in Greenwich Village, an area often associated with fans of Carolyn Bessette-Kennedy, to vie for the title of the most convincing lookalike of the late political figure.
As expected, attendees paid homage to Love Story with boxy suits and fixed-gear bikes, and the event featured more backwards Yankees hats than one could count. Several faithful fans of Bessette-Kennedy arrived in trench coats, embodying a classic, effortless style. Among the crowd, some participants seemed blissfully unaware of their unintentional resemblance to the old-money aesthetics associated with Hyannis Port.
Comparing the real thing to lookalike hopeful Enir Radoncic.
Elena Mudd
“I didn’t even know this was happening,” remarked one participant, casually dressed in athleisure and a backwards hat. This individual, who found themselves amidst the crowd, decided to embrace the moment. Another contestant described the event as the “scariest thing” he had ever done, a sentiment likely shared by many given the throngs of enthusiastic spectators capturing the moment on their iPhones. Contestants arrived in a mix of vintage Hugo Boss and their finest suits, all sporting impressive hairstyles.
Interestingly, many participants credited the women in their lives for their appearances. Numerous wives, girlfriends, friends, and sisters played pivotal roles in styling, encouraging, and ultimately persuading these mostly straight men to don jackets and participate in the contest.

Caress Lourdes and Eddie Klein attempting their best CBK and JFK Jr.
Elena Mudd
As the contest concluded, excitement buzzed around who would emerge victorious. To learn more about the most JFK Jr.-like participants, as well as a few who channeled Carolyn Bessette-Kennedy, follow the latest edition of InStyle‘s On the Grid.







