Apparently, nostalgia looks really, really good on men. Case in point: an unofficial JFK Jr. lookalike contest that popped up in New York City’s Washington Square Park on March 8, 2026. And while no one there could actually pass for America’s prince of preppy, the event made one thing crystal clear—good-looking men in 90s-inspired baseball caps and backwards berets are a national treasure all on their own.
The contest drew hundreds of spectators and participants ready to channel their inner 90s royalty. Think: natural curly hair, casual-yet-polished style, and enough charm to make you forget that none of the contestants were actual JFK Jr. But hey, when life gives you backwards hats and navy blazers, you make it work.
The Winner Who Stole the Crown
At the end of the day, the title went to Julian DeVincentis, who walked away with a $250 prize and, let’s be honest, bragging rights for achieving peak preppy prince energy. Julian sported the classic sleeveless top, roller blades, a backwards baseball cap, and that perfectly casual yet somehow curated JFK Jr. hair flip. We can’t confirm it, but sources say a few hearts were melted, several cameras were broken, and one dog barked in approval. Although, it might be safe to say that outfit and energy aside, lookalike may have been a far stretch–but great job on the vibe!
@jordanataylor The lookalikes just keep getting better and better 🤩 did you get to go to the JFK Jr. one in Washington Square park today? #jfkjr #jfk #carolynbessette #nyc #washingtonsquarepark
The contest was unofficial, but the vibes were 100% real. From sideways baseball caps to low-key blazers paired with sneakers, every participant clearly put effort into channeling that Love Story aesthetic, where John F. Kennedy Jr. meets Ryan Murphy’s glossy, dramatized version of early-90s jet-set romance.
Why JFK Jr. Is Back in Pop Culture
Blame it on the FX limited series Love Story: John F. Kennedy Jr. & Carolyn Bessette, which has taken the streaming world by storm. Available on Hulu and Disney+, the series is officially the platform’s most-watched limited series ever. And fans are not just watching—it’s binge, rewatch, meme, spiral, repeat. Social media is alive with screenshots, reaction videos, and endless nostalgic comparisons between the original JFK Jr. and the dreamy, dramatized version we can’t stop obsessing over.
Even the fashion is making a comeback. The backward beret and baseball cap are trending again, proving that all we ever really wanted was an excuse to rock casual preppy vibes while looking effortlessly hot.
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A Celebration of Style, Charm, and Gay Energy
What makes this lookalike contest so great isn’t just the 90s nostalgia—it’s the energy. It’s playful, it’s cheeky, and yes, it’s very gay. There’s something uniquely satisfying about seeing hundreds of men embrace a shared fantasy of JFK Jr.’s effortless charm, mix it with their own personal style, and serve looks while cheering each other on.
At the end of the day, the contest reminded everyone of a simple truth: you don’t have to actually be JFK Jr. to embody a little prince energy. Sometimes all it takes is a crisp white polo, a backwards cap, and a lot of confidence.
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