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 baseball 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 too.
Seemingly everyone was cosplaying as the couple (fashion-wise) earlier this year, and with fashion being less gender-normative than ever before, it makes sense that we’re all sharing in the trend.
Be it Dua Lipa, Kendall Jenner or Iris Law, each one of these It girls has embraced the backwards hat to give even the simplest summer outfits a more fun, fashion-forward finish. So whether you pull a Kendall and use yours to keep your wet hair restrained post-swim or channel Dua and style it with denim cut-offs, a long-sleeved T-shirt and the instantly iconic Chanel Maxi Flap bag, there’s no denying the backwards-hat styling hack has officially earned its place in the summer wardrobes of the fashion set. Scroll down to shop the best hats.
Shop Caps You Can Wear Both Ways
