Think about the 1960s. Most people jump straight to the Beatles in Nehru jackets or the hippie movement at Woodstock. But there’s a massive, often ignored transition that happened right on top of men’s heads. At the start of the decade, if you walked down a street in Manhattan or London without a hat, people basically looked at you like you’d forgotten to put on your pants. By 1969? Wearing a formal hat was almost an act of rebellion against the new status quo.
The story of 60s hats for men isn’t just about fashion. It’s about the death of a social requirement.
Honestly, the decline of the hat is one of the biggest shifts in 20th-century menswear. We often hear the myth that John F. Kennedy killed the hat by not wearing one to his inauguration. That’s actually not true. He wore a silk top hat to the ceremony. But he hated how they messed up his hair, so he ditched them for the rest of the day. That small act by a global icon gave every other man the "permission" they’d been waiting for to let their hair breathe.
The Trilby and the Fedora: The Last Stand of the Classics
In the early 1960s, the Trilby was king. You’ve seen it on Sean Connery in those early Bond films like Dr. No or From Russia with Love. The Trilby is basically the Fedora's shorter, narrower cousin. It has a stingy brim—usually turned up at the back—and a crown that sits a bit lower.
Why the change from the wide-brimmed hats of the 40s?
Cars.
It’s that simple. As cars became lower and more streamlined, a giant, wide-brimmed Fedora was a nightmare to wear while driving. You’d hit the roof every time you turned your head. The "stingy brim" Trilby allowed a man to look professional while sitting in his Ford Galaxie or Chevy Impala without knocking his headgear into his lap. It was a practical solution to a modern infrastructure problem.
But by 1964 or 1965, the vibe changed. The felt hat started to feel... old. It felt like your dad’s world. While the "Mad Men" aesthetic kept the Fedora alive in corporate offices, the youth were looking for something that didn't feel so heavy and serious.
When the British Invasion Swapped Felt for Fur and Corduroy
The mid-60s were weird and wonderful. As the Peacock Revolution took over London’s Carnaby Street, 60s hats for men became much more experimental. This is where we see the rise of the "Baker Boy" or "Newsboy" cap, but reimagined in wild fabrics.
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John Lennon is the poster child for this. He famously wore the Greek Fisherman’s cap, which suddenly made a salt-of-the-earth work hat look incredibly cool and avant-garde. It wasn't about status anymore. It was about "the look."
These hats were softer. They were foldable. You could toss one in a bag or a pocket, which was something you could never do with a rigid Fedora. Materials shifted toward:
- Heavy corduroy in mustard yellows and deep browns.
- Velvet, because everything in the late 60s had to be velvet.
- Checkered wools that looked like something a 1920s golfer would wear, but styled with a leather jacket.
It’s kind of funny how fashion loops back on itself. The 60s took 1920s working-class headwear and turned it into high-fashion rebellion.
The Bucket Hat and the Casual Revolution
Toward the end of the decade, things got even looser. The Mod subculture in the UK loved a good bucket hat. Back then, they called them "crusher" hats. They were usually made of cotton or Irish tweed.
They were practical for the rainy streets of London, sure, but they also signaled that the wearer didn't care about the rigid corporate ladder. If you were wearing a bucket hat, you probably weren't heading to a law firm. You were probably heading to a record store or a protest. This was the era where the brim size started to fluctuate wildly—some were tiny and almost useless, others were floppy and leaned into the burgeoning psychedelic scene.
Western Influence and the Cowboy Myth
We can't talk about 60s hats for men without mentioning the weird intersection of Hollywood and the counterculture. The "Midnight Cowboy" look brought Western hats into the city. It wasn't the clean, stiff Stetson of the 1950s westerns. It was battered. It was felt. It was worn with fringe jackets.
This was the "Urban Cowboy" before the term even existed. It represented a desire to get back to the land, even if you were stuck in a studio apartment in Soho.
Why the Hat Eventually "Disappeared"
By the time we hit 1969, the "hatless" look was the dominant trend. There are a few reasons for this that historians like Neil Steinberg, author of Hatless Jack, have pointed out over the years.
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First, the hair.
The 60s was the decade of hair. Whether it was the Mop Top or the long, flowing locks of the hippie movement, men were finally proud of their hair. Why cover it up with a piece of felt? If you’d spent an hour getting your hair to look like Mick Jagger’s, the last thing you wanted was "hat hair."
Second, the social hierarchy was crumbling.
Historically, hats were a way to show your rank. A top hat meant one thing; a flat cap meant another. The 60s was all about breaking down those walls. When the youth culture decided they didn't want to look like their bosses, the hat was the first thing to go. It was a symbol of the "Establishment."
How to Wear 60s Style Today Without Looking Like You’re in a Costume
If you want to pull off the 60s hats for men look today, you have to be careful. You don't want to look like you're going to a themed party.
The key is the "Stingy Brim."
If you’re going for a Fedora or Trilby, keep the brim under two inches. Anything wider starts to look like the 1940s (think Indiana Jones or Casablanca). A narrow brim feels more "Rat Pack" and fits better with modern, slim-fit tailoring.
- Pair a wool flat cap with a denim jacket. This avoids the "old man" look and leans into the 60s musician vibe.
- Look for textured fabrics. Instead of plain black felt, try a grey herringbone or a navy corduroy. Texture makes the hat feel more contemporary and less like a relic.
- The tilt matters. 60s hats were often worn slightly further back on the head compared to the forward-tilted "tough guy" look of the 40s. It feels more relaxed and open.
Honestly, the best way to approach it is to treat the hat as a casual accessory rather than a formal requirement. The moment you take it too seriously, it loses that 60s cool.
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Common Mistakes to Avoid
A lot of guys buy a "cheap" Fedora from a big-box store and wonder why they don't look like Don Draper. Those hats are usually made of synthetic materials that have a weird shine to them. They're also often "one size fits all," which is a lie.
A real 60s-style hat should be sized properly. Measure your head. Look for fur felt or 100% wool. The way the light hits the material makes all the difference in the world. Also, avoid the "feather in the band" unless you really know what you're doing. It can look a bit costume-y very quickly.
Real Examples from the Icons
Looking at the archives, certain men just got it.
- Michael Caine in Alfie (1966): He wore the Trilby with such a nonchalant attitude that it felt like an extension of his personality.
- The Beatles: Their early "Help!" era featured flat caps and Greek Fisherman hats that defined the "Mod" aesthetic.
- Steve McQueen: He often skipped the formal hats for a rugged "mechanic" style cap or a simple beanie, which paved the way for the casual 70s.
These guys didn't wear hats because they had to. They wore them because they wanted to. That’s the shift that happened in the 1960s. The hat went from being a uniform to being a choice.
Taking Action: Finding Your 60s Silhouette
If you're ready to dive into this style, don't start with a high-crown Fedora. It’s too much for most beginners.
Start with a high-quality wool flat cap. Look for brands that have been around since the era, like Stetson or Christy’s of London. Look for a "slim" or "duckbill" cut—it’s more aerodynamic and mimics that 60s "Stingy" aesthetic much better than the oversized, floppy caps of the 1920s.
Once you’re comfortable with that, move to a short-brimmed Trilby in a neutral color like charcoal or chocolate brown. Wear it with a simple overcoat or even a clean bomber jacket.
The goal isn't to bring back the 1960s exactly as they were. The goal is to take that sense of transition—that mix of old-school class and new-school rebellion—and make it work for your current wardrobe.
Next Steps for Your Style:
- Measure your head circumference in centimeters to ensure you get a "sized" hat rather than a generic small/medium/large.
- Identify your face shape; stingy brims generally look best on those with narrower or more oval faces.
- Visit a local haberdashery if possible. You need to feel the weight of the felt to understand why the originals were so prized.
- Audit your current outerwear. A 60s hat needs a structured shoulder to look balanced, so see if you have a trench or a tailored coat that fits the bill.
The 60s was the last great decade for men’s headwear before the "baseball cap era" took over everything. By choosing a hat inspired by this period, you’re nodding to a time when men were caught between tradition and total freedom. It’s a great place to be.