Since the recent release of Love Story: John F. Kennedy & Carolyn Bessette on Hulu, the 90s style is back. Or maybe it never left, but it has certainly become more prevalent on my TikTok For You page. The algorithm has decided that America is ready to romanticize camel coats, cable-knit sweaters, and the particular way a man once wore a backwards baseball cap without looking like he was trying too hard.
More specifically, the men and women of America are channeling their inner Kennedy. Women are rediscovering the restraint of Carolyn Bessette’s minimalism. But the men, the men are attempting something slightly more ambitious. They are trying to dress like John F. Kennedy Jr.
Backward hats. Newsboy caps. Soft sweaters layered over crisp white tees. Business casual with those hats. Leather boots. It’s all very intentional in its effort to look unintentional.
Scroll long enough, and you’ll find TikToks of candid men waiting on street corners in SoHo, hands in pockets, cable-knit sleeves pushed up just enough. You’ll find the men of NYC biking in a rather performative way with those fits on. You’ll see slow-motion edits of finance-adjacent 20-somethings adjusting their caps outside dimly lit bars in the East Village, captions reading something along the lines of “bringing back 90s energy” or “outfit inspired by JFK Jr.” The comments are full of praise: “he gets it,” “old money vibes,” “this is the standard.” It is both endearing and a little bit silly.
There is something charming about boys dressing up to go out, trading graphic tees for old money outfits with a backwards hat in hopes that maybe aesthetic effort will signal emotional depth. There is something sweet about the desire to embody a kind of masculinity that feels quieter and more grounded than today’s hyper-performative hustle culture. In a world of LinkedIn self-branding and Instagram thirst traps, the idea of the unbothered, slightly windswept 90s man feels refreshing.
And yet, part of the humor lies in the fact that the outfit is being praised as if it were revolutionary.
A cable-knit sweater is not radical. A backwards cap is not groundbreaking. A well-cut blazer over a white shirt is not a new discovery. What has changed is not the clothing itself, but the mythology attached to it. When John F. Kennedy Jr. wore these pieces, they weren’t simply clothes. On him, they became symbols: of ease, of inherited confidence, of an American princeliness that seemed effortless. And that effortlessness is the key.
The modern recreations are curated down to the cuff. The hats are chosen specifically because they are “Kennedy-coded.” The sweaters are purchased with reference images saved from fan accounts. The look is studied. And while the sentiment is there, while it is genuinely sweet that men are trying to channel a softer, more classic masculinity, they will almost never embody the aura he did.
Because the aura was not just about the fit.
It was timing. It was mystique. It was being photographed candidly in an era before constant self-documentation. It was a pre-social media kind of presence, where you did not perform charm for an audience because the audience was not always in your pocket. It was lineage and cultural myth wrapped into a 6-foot-2 silhouette walking through Manhattan. (And it helped that he was extremely handsome, obviously.)
You cannot Amazon Prime that.
The glamorization of these simple outfits says less about knitwear and more about what people are craving. There is a longing for restraint. For subtlety. For a masculinity that does not announce itself with logos or captions. The resurgence of 90s Kennedy style suggests that both men and women are tired of spectacle. They want something that feels grounded and timeless. And to be fair, the style is timeless. Basics paired casually. Nothing too flashy. Quality over noise. That will always work.
But perhaps the funniest part of this revival is watching men step into bars in New York City dressed like archival photos, silently hoping the cable knit or backwards newsboy cap will do the talking. As if the right hat might summon destiny. As if wearing the uniform of a myth might conjure the myth itself. Clothes can signal taste. They can hint at intention. They can even reshape perception.
They cannot manufacture presence.
So yes, let the boys wear the newsboy caps. Let them romanticize the street corners. Let them bike around trying to emulate JFK Jr. Let them believe that somewhere between a backwards hat and a well-timed glance, they might find their Carolyn. Just know that style can be copied, aura rarely can.