The Best Hats for Older Men
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 . 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. Doyle teardrop fedora
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 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. this classic straw trilby
- 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.
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 Amazon.com:
"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
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.— Hatsinthebelfry.com
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).
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.
- Fedora Felt Hat Guide — Gentleman's Gazette
Learn all about the fedora hat; its history, quality hallmarks, what to buy & what to avoid, and how to wear this great felt hat so you look your best
- Observations on Fedora Sweatbands, Size Tags, and Fedora Dating Tips
Observations on Fedora Sweatbands, Size Tags, and Fedora Dating Tips
- Trilby vs. Fedora: The Difference Between These Hat Styles – Hats in the Belfry
Hats in the Belfry