By Daniel van Voorhis –

Historian Jacques Barzun recalled an event from the mid-twentieth century when he met an old colleague who had recently travelled to Europe. Barzun asked his friend what he had found back in the old country. His friend, despondently, responded: “Communism, and Hatlessness”.

I’ll let someone else deal with the implications of a Marxist/Leninist communal economic system and social order for the good society. For the purposes of this column, I’d simply like to point out two things: Karl Marx was one of the few communist radicals to rock a bowtie, and Lenin had a wicked Van Dyke. Other than that I find their criticisms decently on point, but their solutions wanting.

But, to our real issue: hatlessness. Any old movie star worth his salt had to look good in a hat, perhaps a broad brimmed fedora, possibly a panama hat in the appropriate weather. Consider the choice for women: Jackie O made the pillbox look elegant, a round and tight cloche was a throwback to the flappers, and a vagabond (with a wide brim, one side dipping across the front of her forehead shading the top quarter of her face) gave off a Katherine Hepburn, devil-may-care attitude.

Today, unfortunately, the hat has come to signal two things: pretentiousness or laziness.

We may not win the fight against communism, but perhaps we can rehabilitate the hat.

One reason for doing so would be to return the art of the doff; what ever happened to “doffing”? When you pass an acquaintance on the street you can slide your thumb and index finger knuckle onto the front of your bill, tip slightly, and give a sly “how are you”. Or, you can fully remove it in the presence of a woman to show respect.

There is today, unfortunately, far too much jutting out of the chin, snapping the head back and saying, “sup”.

But, before you rush into the cause of rehabilitating the hat simply to both doff and don, consider:

Your head size and shape

What hat works for what you are wearing, and

Why you choose to wear the hat.

You probably know your waist and shoe size, but do you know your hat size? Click here for a quick primer on head measurements.

Next, what is your facial structure? You might not have the high cheekbones of a young Michelle Pfeiffer or a strong Matt Damon like chin.  That’s ok.  Click here (women) or here (men) to determine what kind of facial structure you have. This matters for things from haircuts to sunglasses and ties, as well.

NOW, what kind of hat are you looking for? You should know the very basic styles:

The Fedora is a standard, and often misunderstood hat. There are so many varieties that a good one is often praised while the poorly chosen is usually pointed out as “a fedora” and mocked. Choose wisely. You should probably have a suit (or at least a shirt and tie) and look for a medium billed, indented top, felt (sometimes leather) classic. You’ll need a slender or long face and a good bit of self-confidence. Please note that the bill can be folded a number of ways. Sinatra wore his flat, Indiana Jones had a distinct back fold. It’s a rangy hat. It might work.

The Derby (or Bowler) is the perfect example of an “if only”. That is “if only” hats were more common you could throw this into the mix from time to time as a type of business casual headpiece. Unfortunately, unless you are shooting for the moon with a retro style or are part of a Laurel and Hardy renaissance, you may want to leave it alone.

The Pork Pie is a short brimmed and low domed hat that was the original hat for all seasons. Wearing an all black pork pie with a particularly flat dome might get you a few “hey Heisenberg” calls, but it can be a standard all weather hat made from felt, leather, straw or a synthetic. Check the brim, material and dome shape and consider helping it make a comeback.

The Flat Cap (or Gatsby) is harder to wear thanks to Samuel L. Jackson, the Kangol brand, and overly self-conscious hipsters. But, a well made and fitted flat cap worn in cold or wet weather can be the understated version of the fedora or pork pie without going straight Paddington bear.

As for women’s hats, if you are covering your head for religious reasons, I’m not mad at you. If you’re at the Kentucky derby or an Easter Sunday brunch, knock yourself out. If you haven’t covered yourself with too many precious accouterments and one type works (and unbiased friends objectively agree), give it a shot.

And then there is the modern baseball cap. It is my hat of choice. My ears make it hard for classic styles to work for me. And, today, wearing both a bow tie and stylized hat is likely to get me dismissed immediately for being too precious. However, the hat shouldn’t be the kind you get for volunteering at the Kiwanis breakfast or the local “5k for a cause”. It needs to be chosen according to the casual colors you wear; it should be a fitted wool version of a team, or specific brand, or a non-ironic snapback. If you go with a sports cap, please make it a team you actually (somewhat) follow, a team from your hometown, or the local team. Always curve the bill and wear it straight forward. Never wear it in semi-formal settings, but rather, wear it for what it is: a stylish way to cover up bedhead, or a way of moving about incognito, or to protect your face from the sun.

In all of this, remember two basic rules: rock it because you like it and it serves a purpose (either utilitarian or aesthetic). As with philosophy, religion, or music, make sure that you don’t just consult those with whom who already agree. Get around other circles and see what they might think; then you may choose to knowingly disregard them.

And always remember the most important rule. If any of these rules make your choice of headwear feel clunky or uncomfortable: break them. But, at least know them first.

All the Best,

The Man About Town

[If you are wondering what an article about hats is doing on this site, check out my first post]

Written While Listening to:

Spiritualized: Ladies and Gentlemen, We Are Floating In Space (1997)