Wearing Hats : 11 Hat Styles For Men

Wearing Hats for Men - by Vintage Cufflinks & More

CLAIM Your Free Style Guide : STYLE TIPS FOR MEN

There was a time when gentlemen would never go out without wearing hats – and we’re not talking about a baseball cap with a football logo. We’re talking about a proper, grown up, sophisticated, stylish hat.

The modern man is once again wanting to look good – dressing up with waistcoats, pocket squares… and wearing hats.

Own one, or have a collection. If you develop a passion for wearing hats, one is never enough. And combined with correct hat etiquette, you will be unstoppable.

A hat is a very suave way to finish off an outfit. It makes a statement. It gets you noticed. Watch some old black & white movies if you want to see how wearing a hat can become second-nature – a totally comfortable extension of yourself.

Ready to learn more about hats?

But there are so many different hat styles, which one do you choose?


Which Style of Hat?

Here are 11 vintage hat styles for men. I’m calling them vintage styles because they have been around for a considerable length of time. That’s not to say they are not a modern fashion statement. Here’s a list of hat styles to get you started.

CLAIM Your Free Style Guide : STYLE TIPS FOR MEN

I’m sure you’re with me on this first one…


Wearing Hats - Trilby Hat Don Draper
STYLE: The Trilby has a smaller brim than the Fedora, and is worn slightly to the back or side of the head. It features a signature crease from front to back, and the brim is slightly upturned on each side. It is made from felt, with a firm but pliable brim.
VERSATILITY: Perhaps the most versatile of the hat family. Wear it with anything from a stylish suit to t-shirt/shorts. Day or night. Flattering to most head sizes.
WHEN TO WEAR: Ideal for the colder seasons, but it can be worn all year round.
ROCKING IT: Jon Hamm, who nailed this look as Don Draper in MadMen.
AMAZON (affiliate link): MIRMARU Classic Trilby Short Brimtrilby hat


Wearing Hats - Fedora Hat Michael Jackson
STYLE: The Fedora is a bit more classic, with a wider brim than the Trilby. It features a signature crease from front to back, and the brim is very slightly upturned on each side. It is made from felt, with a firm but pliable brim.
VERSATILITY: Perfect for a dapper gentleman, a maverick, or a creative. It goes well with a sports jacket, or shirt/trousers combo, or t-shirt and jeans. Check that it suits your head size. Once worn by businessmen worldwide. Stick to neutral tones with a mid-sized brim. Don’t wear the brim down with casual wear. Invest in a quality felt Fedora – it will keep its shape and color over time. Akubra is a good brand.
WHEN TO WEAR: Ideal for the colder seasons.
ROCKING IT: Michael Jackson.
AMAZON (affiliate link): Fedora Hat for Menfedora hat

If I didn’t lose you with the Fedora, keep reading for more mens hat styles…


Wearing Hats - Panama Hat Robert Redford
STYLE: The Panama hat is similar to the Fedora, but is lighter in color and often made from lightweight straw which allows for ventilation. Originally from Ecuador, the Panama hat is associated with seaside/tropical ambiance.
VERSATILITY: Ideal for more casual events. The Panama Hat is designed for warm, blue skies – don’t wear it out of season.
WHEN TO WEAR: The perfect summer hat. Wear it with blue skies.
ROCKING IT: Robert Redford, as Jay Gatsby in The Great Gatsby.
AMAZON (affiliate link): Panama Hat GULLPORT Classicpanama hat


Wearing Hats - Bowler Hat, John Steed, The Avengers
STYLE: Rounded top, with a small upturned brim.
VERSATILITY: All year round.
WHEN TO WEAR: You don’t get more British than the Bowler hat. Commit to the look – double-breasted suit, umbrella, vintage Jaguar.
ROCKING IT: Patrick Macnee, as John Steed in The Avengers (1960s).
AMAZON (affiliate link): Black Blended Wool Derby Hatbowler hat


Wearing Hats - Pork Pie Hat Walter White Heisenberg Breaking Bad
STYLE: A small, round hat with a narrow brim, a flat top and a dip along the inside edge.
VERSATILITY: Versatile across all seasons. Invest in a felt Pork Pie hat. Resist the urge to act like Heisenberg – it doesn’t end well.
WHEN TO WEAR: A casual addition to a weekend outfit (somewhere between a Fedora and a Beanie).
ROCKING IT: Bryan Cranston, as Walter White / Heisenberg in Breaking Bad.
AMAZON (affiliate link): Crushable Wool Felt Porkpie Hatpork pie hat


Wearing Hats - Stetson Hat JR Ewing Dallas
STYLE: A large, bold hat with a wide brim. Widely known as a cowboy hat.
VERSATILITY: Good for protection from the sun or rain.
WHEN TO WEAR: Ideal if you’re sitting on a horse, or from Texas.
ROCKING IT: Larry Hagman, as J.R. Ewing in Dallas.
AMAZON (affiliate link): Stetson Hat Bozeman Wool Felt Crushable Cowboy Hatstetson hat


Wearing Hats - Boater Hat Leonardo Di Caprio Barbershop Quartet
STYLE: A formal summer hat, made from stiff straw with a ribbon around the crown.
VERSATILITY: Usually worn with a lounge suit or casual outfit.
WHEN TO WEAR: A unicorn by today’s standards, seldom worn by men outside of barbershop quartets or posh schoolboy uniforms.
ROCKING IT: Leonardo DiCaprio, as Jay Gatsby in The Great Gatsby.
AMAZON (affiliate link): 2.5 Inch Brim Straw Boater Hatboater hat


Wearing Hats - Newsboy Cap Peaky Blinders
STYLE: Curved brim and puffy eight-panel body with a top button.
VERSATILITY: The Newsboy Cap sits somewhere between a Baseball cap and a Fedora. Invest in a Harris Tweed cap – for it’s indestructability. Don’t get one that is too puffy.
WHEN TO WEAR: Once favored by dock workers and tradesmen, now a trendy accompaniment to suits, shirt/trousers, or a more casual t-shirt/jeans look.
ROCKING IT: Cillian Murphy, as Thomas Shelby in Peaky Blinders.
AMAZON (affiliate link): Men’s Classic 8 Panel Wool Blend Newsboy Hatnewsboy cap


Wearing Hats - Donny Wahlberg Danny Raegan Bluebloods
STYLE: Once a working-class hero, the Flat Cap is similar to the Newsboy but without the button and puffiness.
VERSATILITY: A sturdy, more dressy alternative to a beanie, with far more character. Stick to a wool blend, and stay away from leather.
WHEN TO WEAR: Vintage appeal, easy to wear, for weekend or office attire.
ROCKING IT: Donny Wahlberg, as Danny Raegan in Bluebloods.
AMAZON (affiliate link): Premium Wool Blend Classic Flat Hatflat cap


Wearing Hats - Baseball Cap Mark Wahlberg
STYLE: The Baseball Cap has a snug fit over the head, with a peak at the front – usually with a sports logo. The Snapback Cap has a firmer flatter brim and adjustable back.
VERSATILITY: Comfortable, cheap, and hides the thinning hair. More recently tagged the Dad Cap, for its desirability to middle-aged suburban dads. Don’t wear it with a jacket or suit. Never, ever, wear it backwards. Ever.
WHEN TO WEAR: Only ever in very casual settings.
ROCKING IT: Mark Wahlberg.
AMAZON (affiliate link): Boston Red Sox Men’s Baseball Capbaseball cap


Wearing Hats - Beanie Justin Timberlake
STYLE: A knitted woollen cap, fitting snugly over the head.
VERSATILITY: Sadly, the Beanie has found a place in the winter wardrobe – outside of street-wear.
WHEN TO WEAR: It is becoming common to see beanies worn with suits, blazers and overcoats. Avoid sagging beanies that droop at the back and look like a poorly fitted condom. Get a snug, fitted beanie.
ROCKING IT: Justin Timberlake.
AMAZON (affiliate link): DG Hill Set of 3 Mens Warm Winter Beanie Hatsbeanie


15 Simple Style Changes : STYLE TIPS FOR MEN


Hats Are Back!

A hat is a versatile, functional, suave way to finish off an outfit – appropriate for any season.

“Men’s hats have made a comeback in a big and multi-faceted way. A hat adds that oomph and style that is a small element having a major impact.”
– Gath D’Silva, head of design at The Jacket Maker.

When it comes to wearing hats, you get what you pay for. A quality hat will look good, will make you feel good, and it will last.

A hat will go with almost any outfit, from formal to casual.

Brimmed hats look elegant and also minimize skin exposure to sun damage or provide protection from the rain.

If you’re worried about taking off your hat and forgetting it when you leave, try this – put your car keys inside your hat. You won’t leave without your keys, right?

In sunny countries, like Australia, school children are now wearing hats as part of their school uniform. With early training like that, it’s no wonder hats are making a big comeback. The younger generation are learning that hats are a part of going outside.

Wear your hat with confidence. If it is your first time going out in a hat, brace yourself for comments. Friends or colleagues may be threatened by your heightened style. Their first reaction may be to mock. Be prepared with comebacks. Being confident that your hat enhances your appearance will give you the energy to ride through any mocking. Your hat gives you style and sophistication. All the great Hollywood icons wore hats.

“Hats, to one’s wardrobe, are what throw pillows are to a living room sofa.”

Hats make your outfit look “finished” and polished too. Even a casual outfit looks better with a hat!

Download the free PDF: 11 HAT STYLES FOR MEN

See also:
Wearing Hats: Correct Hat Ettiquette
Ten Classic Mistakes Men Make With Suits
Do You Need Style Help?