Take It From a Woman: I Am Once Again Asking You to Wear Your Baseball Cap Backwards

Way back in the year 2021, TikTok was brazenly thirsting over men wearing their hats backwards. I reported on the viral trend then and agreed with those aroused users, as I still do now: the simple, unpretentious backwards cap is quite sexy.

To understand the modern allure of this laid-back (and arguably uncouth) style, you’ve got to go back to its origins. The backwards cap was first popularized by baseball catchers who flipped them around so the hat’s brim wouldn’t intrude on their protective masks. Then, ‘80s and ‘90s stars like Sylvester Stallone and Will Smith helped usher in its youthful, rebellious connotations.

To put it plainly: athletes are hot, and so are edgy bad boys who refuse to conform to society’s forward-facing standards. The backwards ballcap’s inherent athleticism and defiant nature give the style a level of sex appeal that’s notably higher than its face-shading counterpart. There’s no hiding under a backwards baseball hat — it’s a brasher, sexier look that bares it all. (Not to mention, it’s way easier to make out in.)

Unfortunately, the look gets a bad rap for being “childish” or even “douchey.” When Googling some celebrity style inspo for this piece, the top search results all asked questions in the same vein: Is it okay to wear a baseball hat backwards? Are we too old to wear hat backwards? What is the etiquette around wearing baseball caps backwards?

A year-old Reddit post in r/unpopularopionions argues that backwards caps sported by older men look childish: “Unless the brim is getting in the way of other head gear or vision grown men should NOT be wearing baseball caps backwards … It’s like they’re trying to look like they’re 10 years old and looks immature and ridiculous.”

Admittedly, when you think of older men in backward hats, what springs to mind is probably someone douchebag-adjacent like Limp Bizkit’s Fred Durst, a man likely responsible for the implication that wearing a reversed cap is disrespectful and means you’re a jerk.

But let’s not forget who the actual king of the backward baseball cap is: John F. Kennedy Jr.

I will say, the highlight of penning this piece has to be the long hours of staring at researching photos of a backward hat-clad JFK Jr. hand in hand with Carolyn Bessette. Since Gen Z became obsessed with the old-money aesthetic this past year (think cable-knit sweaters, mansions on the Cape, vintage J.Crew advertisements), photos of the iconic pair and their incomparable style have flooded my TikTok For You Page. And while I have plenty of criticisms of the younger generation’s fixation on the aesthetics of obscene wealth, I too can’t help but be enamored — and inspired — by Bessette and JFK Jr.’s effortless wardrobes.

Obviously, the Kennedy genes were in JFK Jr.’s favor. He could make a paper bag look dreamy. But it was his ability to rock his sporty, unpretentious style with such confidence and ease, in direct contrast to his wealth and famous family (a real knack for a nepo baby), that makes him an enduring dreamboat, even two generations later. Having the confidence to accessorize a suit with a backward hat? Hot. Examining the many, many photos of JFK Jr. sporting a backward baseball cap — on a boat, walking the streets of New York City with his wife or deboarding an airplane — there’s nothing childish or uncouth about him.

When it comes to backward-hat etiquette, there are obvious, implicit dos and don’ts. (Don’t wear one to a formal occasion, like a wedding.) But the next time you’re hopping a flight at JFK, channel the airport’s namesake and move that brim to the back — with confidence.

Not sure what to pair your backward hat with? A few (sophisticated) wardrobe ideas below: