An Explainer on Hats: Why you should and how

Posted on November 7, 2012


Hats and hat wearing are a pretty contentious topic composed of a polarised gentry of dandy types and at the other end of the spectrum, those that believe hat wearing is for douchey show-offs.

Hats: An Explainer

Beginning as a ceremonial garment and then evolving as a protective device against inclement weather, hats served a long and noble purpose as indicators of ranks and status for almost seven centuries, before it was unceremoniously dumped just north of ‘Mad Men’ 1960s. Almost overnight, fedoras and trilbies all but disappeared until recently, because of (or in spite of) Neal Caffrey from White Collar and other sartorialists, hats have been slowly but surely creeping back into the men’s style radar.

Types of hats (courtesy of Paul’s Hat Works)

The Fedora

It has many different personalities even though we are probably more used to Indiana Jones and how he wore his pinched at the front, Paul’s Hat Works has a great explainer on materials that can be used for this classically stylish hat; ready for work or spirited rough housing in search of the lost ark.

Should you wear it? Safe to wear. Rakish.

Douche factor: 1/5. If Indy can, so can you.

The Top Hat

No, it’s not just for magicians and silent movie types. You probably caught the Mad Hatter wearing a variation of it during an episode of Once Upon a Time. It’s a traditional “upper class” hat for equestrian and formal events.

Should you wear it? The world isn’t ready for Abe Lincoln’s return. Wear if you’re a working magician.

Douche factor: 5/5. High unless you pull rabbits out of it later.

The Bowler

The Thompson twins were last seen wearing it in the Tin Tin movie, before that, iconic Bond villian Odd Job used it as a decapitating frisbee. In terms of popular culture, it would seem that the only people to rock a bowler have either strong or comical personalities (ahem Pee Wee Herman).

Should you wear it? Yes. Dandy types would rock this look best.

Douche factor: 2/5.

The Pork Pie

Short flat-topped round crown with a centre “island”, it’s the hat of choice for many gentlemanly musicians including famous Monsieur icon- Frank Sinatra. Now having returned in force to Jazz and Ska communities, the Pork Pie hat ties the Fedora in terms of cultural and sartorial recognition.

Should you wear it? Yes. Rock the Boardwalk Empire look while you’re at it.

Douche factor: 1/5.

The Optimo

It’s a hat tailor made for the tropics. Bond wears one on several adventures, as does Mr. Caffrey, woven Optimos are the predecessor to the Panama. The last iconic character to wear one? Al Capone and that creepy white suited maniac killer alongside him in The Untouchables.

Should you wear it? Are you at the beach? If so, Yes. If no, No.

Douche factor: 1/5 at the beach. 4/5 in the city unless you are named Al Capone or work as his maniac hitman.

Posted in: men's style