Hats, Hats, Hats: A Modern Man’s Guide to Headpiece

Mad Men - Don

When the 35th American President, John F. Kennedy was inaugurated in 1961, he made history in the fashion world with a single act. Not only did he immortalize the saying, “…ask not what your country can do for you–ask what you can do for your country,” but also did away with hats in his first day in office. As the legend suggests, this small act of the former president slowly killed the hat industry.

John F. Kennedy Hat Legend

Suddenly, men of the 60s stopped wearing hats. Some would say that since then, the poor little accessory that kept a man’s head warm has been abandoned in the dark closet.

Bowler and Bowl Cut

From the bowler to the bowl-cut: the evolution of 60s man

Many believe that the days of hats are over. We disagree. Hats are back! Although not back in its glory days in formal wear, it is slowly gaining momentum in the casual wear.

Harry Styles Wearing a Fedora

Harry Styles of One Direction sporting a fedora. Can’t get any hipper than that!

Aside from protection from the sun, warming your head in cold weather, and hiding a bad-hair day, hats are very powerful in building an image. Now let us delve more into the wonderful world of men’s hats. Check out these awesome hats that are hip and classy at the same time.

The Fedora

Bruno Mars' Signature Look

The term fedora was in use as early as 1891. It gained popularity in 1924, after influential man of fashion, King Edward began sporting one. A handful of artists and celebrities have worn it becoming part and parcel of their image.

Michael Jackson's Signature Pose

Guess who?

Bowler, Derby, and Trilby…

These are all variations of men’s fedora. The names are sometimes used interchangeably and there’s only a minute difference between each of them. Trilby hats have smaller brims of no more than a 2″ as compared to other fedoras. Bowler hats, as the name suggest, have rounded crowns. Derby hats were coined as such after an American hatter noticed that many men sporting them are always present in English derby races. So it’s just a matter of nomenclature than style.

Al Pacino in Hat

That hat completes the Al Pacino swagger.


Panamas and Fedoras are confusingly similar. Nonetheless, the rim of a fedora curls up while the rim of a panama hat is straight. More importantly, panamas are often made from plaited leaves of the Toquila plant. Last year, the UNESCO declared panama’s weaving as an Intangible Cultural Heritage of the World.

Sir Ian McKellen in Panama Hat

Sir Ian Mckellen in a panama hat.

The Flat Cap

It is a rounded cap with a stiff brim and a small visor in front. It is traditionally made of wool, tweed and cotton. Just like the Fedora, the flat cap has a number of variations.

Brad Pitt in  Newsboy Cap

Brad Pitt in his signature hat

The Newsboy, Ascot, Flatcap, Gatsby…

These caps belong to the same family where the body of the cap is round and there is a stiff peak in front. It’s okay to get confused with these terminologies, but let’s distinguish one from the other for the sake of posterity.

     1.    The Newsboy;

The Newsboy

     2.    The Ascot;

The Ascot

     3.    The Flat Cap; and

The Flatcap

     4.    The Gatsby

The Gatsby

They differ in the size of the brim, visor and the fluffiness of the body. Now it’s up to you as to which one suits your taste.


Beanies are head-hugging brimless caps that are, more often than not, without any visors. These are perfect on casual wear but be careful wearing them in formal events.

Beckham's Beanie

Give anyone an oversized beanie and a leather jacket and they’re good to go.

MMC Urban Beanie

Urban Beanie from ModernManCollection.com

Hats can build an image. If you want to stand out in a crowd wear something that is not worn by many. You don’t need to always conform to what is trendy and popular. Build up your own style and let others follow suit. These hats might be just what you’re looking for.

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