Skip to main content

The Best Hats for Older Men: Six of the Best

No one wore a fedora like the Chairman of the Board.

No one wore a fedora like the Chairman of the Board.

Six Hats Perfect for Stylish Older Men

All the young dudes wear old man hats. One of the most visible recent style trends is the adoption of old-school lids by hipsters and musicians. Maybe you already know the look—typically a fedora or trilby, often with a houndstooth or subtle check, and almost always worn with a beard. Men of all ages are wearing them, which may be the main innovation: what are now called "old man hats" used to be worn only by actual old men. Not any more.

At 57, I count myself as an old man (and I intend to become a much older man in the years ahead). As such, I have appointed myself to pass judgement on the relative merits of a few of the better "old man hats" you can buy. You are about to read about five of these sweet brims that would look sharp on the style-conscious older man.

The hats in this guide are all very affordable and well made. They're fashion-forward as well as fashion-backward. I hope you enjoy this look at old man hats for actual old men.


1. Doyle Teardrop Fedora Hat

I'm starting out here with the king of the hill—a Doyle teardrop fedora. If you're hip to the classic fedora, this might look familiar to you. The man who steps out in a teardrop fedora, especially on a grainy, rainy city night with cocktails in his near future, is rocking a 100% classic American look. In addition to looking indestructible, this hat is actually crush-proof, weather resistant, and ready to be topped up at any point in the night or early morning. As an older man who is by no means done with the nightlife, I love this lid.

This number has an internal sweat band—not that you ever sweat—and is easy to clean with a clothes brush or clean damp cloth.


  • Classic men's teardrop fedora
  • Hat can be easily surface-cleaned
  • Water repellent
  • Crushable for travel
  • Handmade in Ecuador
  • 100% wool
  • From Borges & Scott

2. Men's Straw Trilby

Here's a summery alternative to the rainy-night fedora featured above. A straw trilby is a warm-weather standby for millions of American men, and it has legions of followers in the UK and Europe as well. Even though this classic straw trilby is really inexpensive, I think it offers a lot more than the low price suggests. These hats are virtually indestructible, age beautifully (like us!), and just have a way of looking "right" perched on the dome of everyone from Brooklyn hipsters to middle-aged mid-western dudes like myself.


  • Imported
  • Breathable, lightweight, comfortable to the touch
  • UV Protection
  • Shorter brim angled down at the front and slightly turned up at the back
  • Hat holder included: keep hats with a perfect shape
  • 30-day quality guarantee please return it within 30 Days and Get Full Refund. Please feel free to contact us if you have any question.
The right hat for the right man can make a solid fashion statement.

The right hat for the right man can make a solid fashion statement.

A person carries off the hat. Hats are about emotion. It is all about how it makes you feel.

— Philip Treacy


3. 9th Street Hats 'Sinatra' Classic Fedora

Of all the hats on my list, this is the one that most perfectly captures that Sinatra vibe. It's cool, dark, classic, and capable of adding another layer of agelessness to any older man's look. If you're an older man like me, you may get a little tired of watching all of these youngsters walking around in their fedoras and trilbys—that's natural! But set this hat on your dome and you'll immediately feel your age, in the best possible way—as a source of power, grace, and wisdom. Not many hats can do that. This one can.

But don't take it from me. Take it from an older man who took the time to review this hat on

"This is my first grown-up hat, and I'm 57 years of age. Looking for something from the 50s look so I took a shot at this hat, and let me tell you this hat is a home-run. I recommend anyone looking for a nice hat -- this is the hat to get."


4. Belfry Gangster 100% Wool Stain Resistant Crushable Dress Fedora

Belfry makes great hats, pure and simple. This one is no exception. It's a solid, classic fedora in 100% wool, stain-resistant and crushable, so when you take it off and shove it in the chest of some goon who's harassing your lady, and when, unfortunately, that goon's blood happens to spill on your nice new brim, it's something less than a tragedy. For you, not the goon.


  • 100 percent wool body is soft, warm and perfect for cold-weather wear
  • Offers excellent water and stain resistance
  • Grosgrain sweatband to wick sweat and hold hat's shape
  • Stylish 2 3/8-inch brim and a 4-inch C-Crown
  • Crushable, packable design that bounces back to its original shape after long trips

...and when, unfortunately, that goon's blood happens to spill on your nice new brim, it's something less than a tragedy. For you, not the goon.


5. Belfry Striped Crushable Wool Trilby

Another wickedly cool Belfry hat, perfect for the older man. Everything that is detailed in the description above applies to this hat as well. A great hat for a great man (you know who you are).


Trilby versus Fedora: The fedora has a movable, or “snap” brim; the trilby, on the other hand, is made so that the brim is permanently fixed down, and usually the brim is set at a much more severe angle than the fedora.


6. Brixton Men's Messer Medium Brim Felt Fedora Hat

Finally, we finish up with a classic fedora. Nothing fancy, just a hat that I think is awesome, and would be an amazing addition to any older man's closet. Going out into the world demands a level of attention and energy that many older men are unwilling to devote, but you and me, we're different. Put this hat on your old man head and get out there—the youngsters need to see a confident, sexy, powerful old man wearing their style like it should be worn.

Humphrey Bogart's fedora in "Casablanca" defined an era.

Humphrey Bogart's fedora in "Casablanca" defined an era.



harshita bhawnani on June 02, 2020:

your blogs are very interesting

Ed Palumbo from Tualatin, OR on October 10, 2019:

I should comment, hats made of fur felt are different than hats of wool felt or straw; they're built to last (and priced accordingly). I've gotten more than 10 years of wear from my fur felt Stetsons and they "age" with wear and time. One became a chew-toy for a guest's dog, much to my dismay, and these things happen. Another was blown into a creek by a powerful gust, and that hat was like an old friend. There are different grades of fur felt but one does well to begin with a wool felt hat to see if it's a good fit for one's personal style. Fur felt is more of an investment; however, if you spend a fair amount of time outdoors, a hat will serve you well.

elnavann from South Africa on October 10, 2019:

Hi. I love these hats: an understatement rather than attention-seeking

Ed Palumbo from Tualatin, OR on October 06, 2019:

I'm 73 and keenly aware that hats as a fashion accessory fell out of style with the Kennedy administration; however, I live in the Pacific Northwest and we have WEATHER in my corner of the woods, so a hat is a practical wardrobe accessory, if only to keep the rain from falling on my "solar panel".

I typically wear city hats (fedoras by Stetson) or country hats (Open Road by Stetson and Resistol). The fedoras have enough of a brim to shade your eyes and are creased fore and aft, while the "western" hats have a wider brim and whatever crease you want. When I was young(er), most restaurants had hat racks or hooks because hats were typicallt worn. Today, you'd be hard-pressed to find somewhere to hand your hat, even in an upscale restaurant. Doesn't matter - I wear 'em anyway. I'm told a fedora makes a statement these days but I haven't defined what that statement may be. We get a fair amount of rain in the Pacific Northwest and the feeling of rain on my bald head is like icewater on a bowling ball. Should rain creep down the back of my neck...that's intolerable. My daughter long ago classified my hats as city/country and I can't disagree with her. A hat with a brim is best worn by a man with some character in his face. If a young man wears them, he looks like he's wearing his father's hat. A hat makes sense to me, and I can't say with certainty that they're making a comeback but I have four or five that are part of my wardrobe. Let others make choices as they wish.

Doris James MizBejabbers from Beautiful South on October 05, 2019:

Nice presentation, GreenMind. Somehow I've never liked hats on men unless they were being worn for warmth or to cover up baldness. My dad never considered himself "dressed" unless he had on a hat. He had a nice head of hair all his life, so I've always wondered why. Just the style of the times (midcentury), I guess. Back then they referred to their hats as fedoras.