It Girls Are Having a JFK Jr Summer—This Styling Hack Will Instantly Update Your Look in 2026
Our take
The cyclical nature of fashion is a constant source of fascination, and the current resurgence of a backwards baseball cap – particularly its association with a “JFK Jr. Summer” aesthetic – exemplifies this beautifully. It’s a trend that feels both undeniably nostalgic and surprisingly fresh, a testament to the power of cultural memory and its ability to reinterpret itself for new generations. The initial dismissal of caps as a traditionally masculine accessory, as noted in the piece, is a common narrative within fashion – a barrier broken down by individuals who intuitively understand that style transcends arbitrary gendered boundaries. Seeing Gen Z embrace this look, after years of it being perceived as outside their realm, highlights fashion’s ever-shifting landscape and the way younger generations are actively redefining and reclaiming past trends. The reference to [Spotted at the Airport: The 5 Coolest Luggage Trends of 2026] underscores this broader movement towards effortless, travel-inspired style, where practicality and aesthetic appeal seamlessly converge.
This isn't simply a revival of a single item; it’s a deeper cultural shift – a yearning for a perceived era of understated elegance and effortless cool. The "JFK Jr. Summer" moniker references a time often romanticized for its blend of intellectualism, understated style, and a certain inherent optimism. While the reality of that era was undoubtedly complex, the aesthetic – clean lines, classic pieces, a hint of rebellion – resonates strongly today, particularly as a counterpoint to the maximalism and overt branding that have dominated recent trends. It’s a move towards quiet luxury, a concept we deeply appreciate, where quality and intention speak louder than logos. The willingness to re-examine and appropriate elements from past decades, as demonstrated by the article’s focus on this seemingly simple styling hack, speaks to a growing sophistication within the fashion consumer base – an understanding that style isn't about chasing fleeting novelty but rather curating a personal narrative through considered choices. Interestingly, the piece’s mention of bidding adieu to summer trends and looking towards fall, as covered in [I'm Bidding Adieu to Summer Trends—19 Nordstrom Anniversary Sale Pieces Trending for Fall], illustrates how these cyclical trends are constantly evolving, adapting to the changing seasons and consumer desires.
The key to this trend’s staying power lies in its versatility and accessibility. A backwards baseball cap can be paired with everything from a tailored suit to a simple sundress, offering a playful juxtaposition that elevates even the most basic looks. It’s a styling hack that embodies the spirit of effortless cool, a concept that feels particularly relevant in an age of carefully curated online personas. The recent reimagining of classic pieces, as seen with Sofia Richie Grainge's "cool-mom" groutfit featuring Chloé sneakers and a Balenciaga bag, as detailed in [Chloé Sneakers and Balenciaga's Le City Bag Give Sofia Richie Grainge's Sweatpants Look a Cool-Mom Makeover], further reinforces this trend of blending high and low, casual and sophisticated. This ability to transcend traditional style categories is what makes the backwards baseball cap not just a fleeting fad, but a potentially enduring element of the modern wardrobe.
Ultimately, the resurgence of the backwards baseball cap and its association with a romanticized past signals a broader desire for authenticity and understated elegance within the fashion landscape. It’s a trend that prioritizes feeling over flash, a quiet confidence that resonates with our ethos of self-assured style. The question now is: how will this aesthetic evolve as it’s absorbed and reinterpreted by each new generation? Will it retain its association with the “JFK Jr. Summer” ideal, or will it forge its own distinct identity, shaping the future of style in unexpected ways?
Many fashion trends feel like a quick fad, a blink-and-you’ll-miss-it moment of fun. This is what I thought would be the case with the backwards-hat trend. For years, I, like many of the Gen Zers on my TikTok For You Page, thought that caps were more of a "man" thing.
Think Justin Bieber strolling through L.A., open shirt with a pizza box in hand, using his cap to keep his floppy blonde hair at bay. Or Tom Holland opening a car door for Zendaya, looking less like your Friendly Neighbourhood Spider-Man and more like the internet's ultimate boyfriend. On men, a backwards cap radiates a nonchalant sex appeal, but this summer, after spotting many of my favourite celebrity It girls embracing it, I knew it was only a matter of time before the backwards hat became a bona fide trend amongst men and women alike.
To understand the enduring allure of the backwards cap, you’ve got to go back to where it all began. Originally worn by American baseball catchers (the cricket version of a wicketkeeper), they'd flip their caps backwards as a practical solution to stop the brim from interfering with their protective masks. Then, in the '80s and '90s, wearing your cap backwards became less about function and more about looking cool.
Brad Pitt, Tom Welling, Tupac Shakur and prime-time Becks: each made the backwards cap their own, evolving its purpose from straight-up athleticism to one etched in bad-boy charm. There's nowhere to hide when you wear a cap backwards—your face has to do the talking.
I’d argue it was Friends that turned wearing your cap backwards into a styling hack for women, too. I mean, it's impossible to think of American football without picturing Jennifer Aniston’s Rachel Green rugby-tackling Matt LeBlanc's Joey Tribbiani with two pigtails under her black backless cap.
Fast forward to 2026, and the trend has been given a new life after FX released the hit TV show Love Story: John F. Kennedy Jr. and Carolyn Bessette on Disney+, and a younger generation was not only given a snapshot into their (dramatised) love life, but their fashion sense too. Whilst we’ve covered the formidable force of fashion that was CBK at length, her other half (who lived in backwards Kangol flatcaps and baseball hats) deserves credit where credit is due.
With cosplaying as the couple (fashion-wise) at an all time high earlier this year, and fashion the least gender normative that it's ever been, it makes sense that the girls are “borrowing from the boys” this summer, and make it cooler than ever.
Be it Dua Lipa, Kendall Jenner or Iris Law, each one of these It-girls has embraced the backwards hat as a way to give even the simplest summer outfit an edgier, more fashion-forward finish. So whether pulling a Kendall and using yours to keep wet hair restrained post-swim or channelling Dua and styling it with denim cut-off shorts, a long-sleeved t-shirt and the iconic Chanel Maxi Flap bag, there's no denying the backwards hat has officially earned its place in the wardrobes of the fashion set this summer. Scroll down to shop the best hats below.
Shop Caps You Can Wear Backwards and Forwards:
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