At the JFK Jr. lookalike contest in Washington Square Park on March 8, 2026, the outfits ranged from tailored suits and backwards hats to short shorts, sneakers and roller skates. The reported looks mixed the clean-cut prep associated with John F. Kennedy Jr. with sporty and comic touches.
What contestants wore in New York
InStyle’s March 9 street-style report captured the contest’s range: one contestant wore short shorts with New Balance sneakers; another wore a quirky vest, a hat and drawn-on chest hair. The winner stood out in roller skates. InStyle’s event report documents these specific looks.
A CBS News New York video description adds rollerblades, suits and backwards hats to the mix. Together, the accounts suggest a visual contrast between tailored, polished outfits and playful athletic or costume-like choices—not a uniform dress code. CBS News New York’s description identifies those additional elements.
How the hats fit the JFK Jr. look
Headwear was part of the contest’s look, with backwards hats explicitly mentioned in the New York event description. But the available reporting does not identify specific hat brands or models, or establish that one style defined the contestants.
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Before the event, Time Out New York described the target as clean-cut prep, easy confidence and perhaps aviator sunglasses. That was a preview of the intended aesthetic, not a report that every attendee wore those pieces. The actual event coverage records a broader, more irreverent mix. Time Out’s preview sets out that expectation.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Prep styling met playful interpretations
The outfits made the contest’s fashion appeal less about reproducing one exact look than about reworking its familiar cues. Suits and hats offered the polished, preppy side; shorts, sneakers, skates and drawn-on chest hair pushed toward athletic humor and costume. The reports describe what people wore, but do not establish a formal fashion judging rubric.
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A Washingtonian account of a separate contest in Washington, D.C., mentions backwards newsboy caps, baseball hats and a beret. Those details belong to the D.C. event, not the New York one, and should not be read as a list of hats worn at Washington Square Park. Washingtonian’s report provides that separate-event context.
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