In the 1940’s when men were men and women were dames, the “Panama” Fedora was the gentleman’s hat of choice in sultry climes and classic films. It remains the most popular style today.

There are many style variations that are all called Fedoras. I offer five different Fedora styles of Montecristi Panama hats.

The Classic Fedora is my personal favorite. It is, to me, the most elegant, most classic of all. (I especially like the tear-drop-shaped “island” in the top of the crown.) This is the style I wear personally about seventy-five percent of the time.

I designed the blocks (that give the hats their shape) for this particular style myself. I wanted to keep the classic styling while giving the hat a less “blocky” look than was the norm in the ’40’s. I’ve reduced the space between the “dimples” in front and have given the hat a slimmer, more tapered look.

Judging from the number of compliments I receive when wearing this style, and from all the happy emails and phone calls from customers who like what they’re seeing in the mirror, I think it’s safe to say that people like the look.

You can wear this hat with anything. Shorts, jeans, designer resort wear, even a business suit. If you’re buying your first fine Panama hat, or if you’re only likely to have one Panama hat, you should give serious consideration to the Classic Fedora.

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November 12, 1959. My parents were out, so I answered the phone myself. The connection wasn't good. Some man said he was calling from Cuba, and his name was Hemingway. Who? I was still reading the Hardy Boys. I was ten years old.

“Listen, kid.” He called me “kid.” Kids hate to be called “kid.”

“You don't know it yet, but you're going to make Panama hats someday. You're going to be good at it, so let me tell you what I want. When you're ready, make it for me.

“I do NOT want one of those bright white Reginald-at-the-club-looking things. Hell, I don't even want it to look new. It should look like it's been somewhere, like it has stories to tell.

“Make it a fedora. Pinches in front. Teardrop-shaped island in the top. When you block it, go easy. I don't want it all crisp and ironed looking. Don't worry about it. I want it to lose the shape you give it, as it takes the shape I give it. It should be shaped by life, by experience, by the occasional careless handling, by being too dumb to come in out of the rain once in awhile, by a bottle of Havana Club and some rummy idea about what a brim should look like, maybe even by thoughtless idiots who don't know enough to keep their damn hands off another man's hat.

“Don't be stingy with the brim. Give me some shade. A proper Panama should have a brim that sticks out farther than the end of my nose, not as far as the end of my cigar. Turn it down in front. Drink, smoke, and cuss while you're making it.

“Don't make it until you're ready. If I'm not still around, make it anyway. There will always be men who need a good hat while they're getting on with getting on. And if women want one, too, so much the better. I can't think of one damn thing that doesn't look better on a woman than on a man.”

He said goodbye and hung up.

I said, “That was weird,” and didn't tell my parents. They probably would just think I'd found the key to the liquor cabinet. I had, but that's not part of this story.

Thirty years later, I started making Panama hats. The first style blocks I designed were the style he described. I called it the Classic Fedora. It was too late to make one for Hemingway, so I didn't rush into it. But I'm ready now to make one for you, if you need a good hat while you're getting on with getting on.

The story above is a dramatization of an event that never occurred.

Important Stuff:

Style:
Same style as my Classic Fedora.
Blocked on exactly the same blocks.

Prices:
One or two levels below a Classic Fedora
with the same weave count.

Why Lower Prices?
These are older hats and/or have irregular brim edges, spots, areas of darker straw, maybe some broken straw, anything that would disqualify it from being one of my regular Classic Fedoras.

Some might call them seconds. Others might say they have character.

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“Who wants to go to town?” demanded Daisy insistently.
Gatsby’s eyes floated toward her.
“Ah,” she cried, “you look so cool…You always look so cool,” she repeated.

F. Scott Fitzgerald,
The Great Gatsby

Fitzgerald never revealed exactly what sort of hat Gatsby wore. But we know Gatsby, so we know his hat would have been elegant, distinctive, stylish, expensive, the envy of all who didn’t have one just like it. Well, envy no more; I give you—The Gatsby.

My Gatsby Fedora is a totally custom design. To make one requires two completely different blocks, an unreasonable amount of individual hand-work, and a couple of personal trade secrets. To wear one requires simply that you have a good head on your shoulders.

The Gatsby has a slightly taller crown, wider brim, wider ribbon, deeper “dimples” than my Classic Fedora. The top of the crown has a distinctive center crease.

The Gatsby is especially appropriate when driving your Bugatti to the club, drinking rum beneath a slowly turning ceiling fan, doing anything with palm trees nearby, or just looking like a man who looks great in a Panama hat.

That’s Bruce in His Custom Gatsby

Bruce comes over Friday afternoons to help me guard the lake.

My back yard borders a decent sized lake. It makes for a nice view, framed by two palms and a mango tree. I would hate to lose it. So Friday afternoons Bruce and I sit out back and watch the lake to make sure no one steals it. We also make sure several cold beers were not brewed and bottled in vain. Clearly, we are Men of Conscience.

Bruce’s custom Gatsby is a long oval. Half way between 7¼ and 73⁄8. The ribbon is Chocolate Brown.

Ya gotta love it. That’s my buddy Bruce sitting in the backyard wearing a red T-shirt and his custom Gatsby. The man looks like he could be sitting in the Director’s chair of a multi-jillion-dollar movie set. (I’m glad he wasn’t. He’s easier to talk to when he’s in the back yard.)

Should you have your hat custom-made? Look at Bruce. When the man defines the hat, the hat defines the man. © BBB

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The Optimo is the classic Panama hat style. In Ecuador, it’s called the Natural. The Optimo was the style of choice for British travelers, ex-pats, and empire builders in Malaysia, Hong Kong, India, and throughout the tropics—anywhere a gin and tonic had actual therapeutic value (against malaria, not just tropical tantrums). Even today, the style is more popular in the UK than in the US.

Some people think of it as a “Charlie Chan” hat. I preferred it on Peter O’Toole in The Last Emperor, Sean Connery in The Man Who Would Be King, Sidney Greenstreet in Casablanca.

This style probably originated as a natural consequence of people rolling up their hats. If you roll up an unblocked hat a few times, you wind up with a center crease. So why not call it a style, give it a name, and make some blocks.

This particular Optimo is hand-blocked and has a leather sweatband. You don’t roll it up. If you want one to roll up, go here: Foldable Panama Hats

As with fedoras, there are several variations of the Optimo style. And as with Fedoras, I have definite opinions so I designed my own blocks. I prefer a more rounded crown over a flatter crown. Why? Better looking. Also better architecture.

The Optimo has been growing in popularity. More and more of you are choosing to swan about in non-roll-up Optimos. My friend, Roff Smith, wears his Optimo as his Writing Hat. As his Travel Hat. As his Going To Town Hat. As his Going To The Swings With Daughters Hat. And so on.

A good hat is like that. A good hat becomes a good friend.™

Visualize having ten good friends.

Now make it so.

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The 1930s and 1940s were a golden era for Panama hats. I love the movies: Casablanca, To Have and Have Not, Mr. Moto, Charlie Chan, film noir, The Thin Man series, and many, many others. During Hawaii’s celebrated Boat Days, before commercial air service to the islands, the arrival of a cruise ship was a big deal and, looking at the photos, one might think Panama hats were required attire to greet the ships.

This particular style of Optimo was one of the most popular choices. Compared to my standard Optimo, the 1930s Optimo is flatter on top, less of a dome. The transition from the top to the side of the hat is more abrupt, not a continuous curve.

Sydney Greenstreet favored this look in Casablanca and other movies. Charlie Chan in Charlie Chan in Panama. US President Franklin Roosevelt and many other public figures also wore this type of Optimo.

It’s a very different look than the Optimo style I have offered for more than 20 years. Even the ribbon and bow are different. ¾-inch Classic Black ribbon in a retro bow treatment. I think of it as a Col. Sanders bow. (FYI: I am a for-real, certified-by-the governor Kentucky Colonel, and I have one of those ties. I sometimes wear it on Derby Day.)

Which do you prefer? The original round dome Optimo, or the flatter 1930s Optimo?

Good choice. Now click the Order button for that one.

If you want one you can roll up, go to Rollable 1930s Optimo

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Time lost its job three days ago. Fired. You left the airport in a ’54 Coupe DeVille taxicab and you left the known world in a distant memory bank that no longer allows withdrawals.

¡Bienvenidos á la Habana!

The bar you’re in looks like a movie set. Except it really is old and authentic, not just made to look that way. One of the three ceiling fans turns at half speed. Nice touch. You asked about rum, you learned about 20-year-old estate bottled Havana Club. Legs like a Rockette. Goes well with Cohiba Robustos. Sip slowly. Forget the lime juice. Bring on the bulls.

Old locals nod to you. Here, and everywhere else you’ve been. They don’t nod to other tourists. At first you kept looking behind to see who they were nodding to. You finally figured it out.

It’s the hat.

I love classic styles. I’ve wanted to offer this style for years. I finally found some blocks that have just the right pinches, just the right center dent, just the right vertical taper on the sides of the crown, and just the right front-to-back profile curve on top of the crown.

So this must be just the right time to order one.

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People sometimes ask me “Is this really the style of Panama hat that wealthy celebrities like Errol Flynn and Noel Coward wore when they disembarked from their private yachts in Jamaica and other Caribbean islands during the 1940’s and ’50s?” Well, if it wasn’t perhaps it should have been.

The Montego Bay is another classic fedora style Panama hat. It is equally appropriate for disembarking from yachts in the Caribbean, seaplanes in private bays, golf carts at the club, or lounge chairs by the pool. Some have suggested that wearing the Montego Bay while drinking a piña colada improves one’s chances of seeing the green flash as the sun winks goodbye in the tropics. I think more research needs to be done. Any volunteers?

Do you see how the Montego Bay Fedora differs from the Classic Fedora at the top of the page? Compare the profiles. The Montego Bay is proportionately taller in front and lower in back. In the top of the crown of the Montego Bay, the “island” is a little less teardrop shaped, a little more diamond shaped.

If you want a skinny-brim hat, this is a good style to work with.

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Key Largo, the movie, is an absolute classic. Bogart. Bacall. Palm trees. Panama hats. Who could ask for more?

Well, maybe Bogie could have been the one wearing the great hat. Instead of the relatively minor character Toots. Toots was one of the tough guys with Johnny Rocco (Edward G. Robinson).

Toots wore a fedora. Same shape as my Montego Bay Fedora, but with a distinctive difference: a little raised crease line running vertically up each side and the back of the hat. The crease line in front is a little wider, which is what it should be.

Toots wore his hat in the bar, and in the hurricane. He and the hat looked better in the bar than in the hurricane.

So, when you wear your own Key Largo- That’s the obvious, perfect name for the style, right? Most of us would rather wear a “Key Largo” than a “Toots.”

When you wear your own Key Largo, favor bars over hurricanes. And especially favor bars near beaches, swimming pools, palm trees, in country clubs, island-bound airplanes, and tropical resorts.

TIP: If you are wearing your Key Largo and decide to roll into a hammock and have a little nap, take off your hat!

Put it over your face (good for shading the eyes and looks good in ads), or put it on your chest. If you leave it on, you will wreck the brim. You knew that? Okay. Good. Sorry. I take it personally if you wreck my hat.

You probably can guess what size I made the very first Key Largo, the prototype. My size, of course.

Love it. Nearly wore out three mirrors.

I didn’t go with the Classic Black ribbon, as Toots did. Can’t go wrong with a black ribbon on a Panama hat. But some of us like something a little less formal, a little more cheerful, a lot more island attitude.

I decided on Caribbean Blue. What color is perfect for you?

No. Don’t go there. Ribbons are not changeable. Wish they were. But I am a nutcase for best possible everything. So ribbons are hand sewn with special thread, great skill, rare patience, and often spiced (I’m told) with blasphemy practice for Talk Like a Pirate Day.

When you wear your own Key Largo, it’s definitely okay to imagine yourself as Bogie’s character, instead of Toots.

In fact, I encourage it.

The Classic Fedora has been my most popular style for more than 30 years. And the Classic Fedora Island Style is the most popular of the “open weave” styles. If you wear one, you also will be popular.

Many years ago, I made a personal hat with this diagonal weave pattern. It got compliments every time I wore the hat. So, I had more hats custom woven with this same pattern. Why should I be the only one getting all those compliments?

Just in case you’ve never seen this type of weave close up, the dark areas are spaces between the straw. The light areas are the straw itself. Serious ventilation. Almost like having an air-conditioned hat.

Montecristi hats are famous for being woven of very thin (fine) straw. So they are lighter weight, thinner, and less “firm” than most Panama hats you may have experienced. The open weave crowns have about half as much straw as a solid weave Montecristi hat. So, they are even lighter weight, even less “firm.” I do put a little stiffener in the straw so they will hold the shape better, but I don’t make them stiff. (If you want it stiff, just ask.)

Crown heights and brims widths vary. Minimum crown height is 4 3/8 inches measured on the side. I generally aim for about 2 1/2 to 3 inches of brim width. If you have a specific brim width in mind, let me know and I’ll see if I have a hat that will block to your size, and will also have the brim width you prefer.

This is a very cool style. Both literally and figuratively. By wearing one, you also will be very cool.

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Kentucky Smith_® may not be as famous as that Jones guy from across the river in Indiana, but he wears a better-looking hat.

There are other differences. Kentucky Smith_® maintains a totally tropical state of mind at all times, in all places. Almost like a religion. Makes Jimmy Buffett look like Nanook of the North.

In Tibet, Kentucky’s unusual wardrobe choices won him the awed respect of local lamas, who could clearly see the challenges of white linen shorts and vintage rayon Hawaiian shirts at 18,000 feet. Very Zen. Naturally, he wears a Panama hat. Always the same style.

When he’s in town for business meetings, he wears a Montecristi hat like the one shown here. He has eight. Various qualities. Why take a chance? Have backups.

When he’s adventuring around in the unpronounceable parts of the world, he wears the Safari Edition of this style.

Which version you choose (consider both) depends on which sort of adventures you expect. Or want.

If you’ll be riding over paved highways in a Mercedes, BMW, citified Range Rover or Hummer, on your way to a meeting with bankers, attorneys, or your wife, go with the Montecristi version.

If you’ll be riding over the Silk Road on a camel, donkey, or your own two feet, on your way to a meeting with warring nomad chieftains in the Hindu Kush, the Safari Edition probably makes more sense.

Look at the pictures. Great style. You can see for yourself you’ll be in the middle of some sort of adventure within an hour of putting it on. You’ll be the one whose hat everyone envies.

You don’t have to own one to wear one. A plantation, that is. But if you do own a plantation (or horse farm or ranch or maybe even just a really big yard), here’s your hat.

This may not be your working hat, mind you. You might want something a bit less fine for actual physical labor. But after the cane is cut or the cotton is picked, and it’s time to sit back and enjoy the fruits of your labor, perhaps with a rum punch or mint julep in hand, this is the hat to be sitting under.

Wide brimmed straw hats have shaded planters from Mississippi to Manila to Mombasa since time immemorial. Rarely have those hats been as finely woven or as impeccably styled as this one.

You may have noticed that my Plantation style hat has the same pinches in the front and teardrop-shaped island in the top of the crown as the Classic Fedora. I make both styles on the same blocks. Only the brims are different.

If you like the look, but feel a little too conspicuous wearing a wide-brimmed hat, consider a Plantation with a Fedora-width brim, 3 inches or less. That’s been my personal preference over the years.

Either way, the Plantation definitely makes a different statement than the Fedora. And offers a bit more shade.

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The Aficionado style was originated around the turn of the century (2000) by Master Hatter Trent Johnson of Greeley Hat Works. Some say that a Plantation and a Fedora got to fooling around in his back room. One thing led to another, and an Aficionado was the result.

Could be.

The Aficionado brim is wider than a Fedora, usually not as wide as a Plantation. The brim is curled like a Plantation for about three-fourths of its circumference, and turned down in front like a Fedora. The crown is the same as both parents.

It’s quite a nice look and has been very popular since its birth a few years ago. Many now favor it over the Plantation.

The Aficionado can give you a little more portable shade than the Fedora. Some say it can look a little more dressy than the Plantation. Others say it has a more Western look than the Plantation.

It can provide you with the perfect choice if you just can’t make up your mind between the Fedora and Plantation. Or if you just like the look. Many do.

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This is the original Planter style, as immortalized by Clark Gable in GWTW. Charlton Heston wore a very wide brim version in his portrayal of a South American plantation owner in Naked Jungle. His wife (Eleanor Parker) looked even better in hers.

These days, the most common interpretation of this style is usually called a “Gambler.” And because most of them are shaped on a hat press, the outer edge of the brim just sort of turns up.

My Monte Carlo is blocked and styled by hand, so the brim edge gets a full curl. That’s the way they made them when there really were plantations and riverboat gamblers. And that’s the way I make my Monte Carlo now. No short cuts.

You can change the look of the style to suit your look by having me make your brim wider or shorter, and by making the curl diameter bigger or smaller.

Brim width can vary from about 2¾ inches to 3½ (after the curl). Curl diameter can vary from about ¼ inch to about an inch. Send me an email or call if you want help deciding.

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This has been a very popular style for many years. I used to call it the Golf of Panama. (Small joke on Gulf of Panama, and a good style for golfers.) Now, I’m welcoming the style to the family of Island Style styles and renaming it accordingly.

This is an absolutely classic Panama hat style. Think Clark Gable in GWTW. Perhaps Mr. Gable would have preferred the open weave and better ventilation of the Island Style version had it been available, especially while escaping the inferno of Atlanta burning. That would have been much hotter than an August afternoon in Atlanta today, even factoring in global warming.

It is a truly great style for golfers. Good sun protection, good ventilation, and very good looking. Some clients swear the Monte Carlo IS takes at least five strokes off their game. I’m inclined to believe them.

Not a golfer? No worries. Unless you have a personal prohibition against looking great, this is an excellent choice for men or women.

Geometrical patterns vary, but they are all attractive, so no need to fret over what I might choose. I generally choose whichever hat will block to your size, and will also have the brim width you prefer.

As you can see, this is not just a hat – it’s Art. The artists of the small village of Las Lagunas, in Montecristi Canton, weave the straw into geometric designs. Like snowflakes, no two are exactly alike. I’ve watched them do it, and I still don’t believe it’s possible. They assure me it is, and keep weaving.

Prove it to yourself by ordering one.

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You might think from the name that Sidney Greenstreet wore this style. He didn’t. But he would have if I’d been around then. I’d have said “Sidney, put this on. There. Now look in the mirror. See what I mean? Next time, Sidney, you get the lead instead of Bogie.” Perhaps wearing this style would have made his illustrious career even more so.

There is still time for you.

An Optimo crown with a wider pencil-roll brim. Odds are, no one else at the party will be wearing this style. If there really is someone else wearing this same style, go say hello. You probably have a new best friend.

One small caution. This is not the style to wear if you do not want to be noticed. The Greenstreet does not exactly blend in. If you’re a private detective following someone and you don’t want them to see you, leave the Greenstreet at home.

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This style was created for a client who lives on a tropical island off the coast of China. He didn’t say whether he has it all to himself. He did say the sun is strong.

He wanted a special style. One he could wear to the club for lunch or to Hong Kong for a meeting. Elegant without being formal. A style that would look good with a cigar.

After some discussion, we agreed on a Monte Carlo crown. After some experimentation, we agreed on a relatively short Aficionado brim. As soon as we saw the combination we knew it was a winner.

Fortunately for Andy, he’s not my size. If this hat had been my size, I would have been sorely tempted to start on a new hat for Andy. The moment I stepped back from the finished hat to take a look, I wanted to put it on and go watch thoroughbreds thunder down the home stretch at Keeneland on an Indian Summer afternoon perfumed by horses, bourbon, and burgoo. But that’s just me. Andy probably took it out of the box, put it on, and went to the beach.

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Have you met Marcie Polo? You’ve heard the stories, right?

Marcie is the great, great, great, great, great, great — well, she’s really great –– granddaughter of Marco Polo.

She is an international enigma, with an overdose of excellence in multiple skill sets.

Marcie “invented” this style in order to prevent a war. She’s like that.

She was called in to mediate a merger between North Unsteadistan and South Unsteadistan.

Not a lot of job security working for one of the Unsteadistans. No point asking about a twenty-year pension. Twenty months is a long tenure for an Unsteadistan government. One lasted less than twenty minutes.

Marcie stipulated they pay in advance.

Parliaments of both nations had voted long ago to merge the two nations into one. Everything went surprisingly, perhaps shockingly, well for many months.

They agreed on the shape of the negotiation table after only five months of debate.

They agreed on a new flag, new national anthem, national capital, national bird, tree, flower, gem, holidays (first item on the agenda), and almost everything else. Then it all came off the rails.

They couldn’t agree on the official national hat.

One popular proposal had been a soccer ball. Fully inflated. The rationale was that a soccer ball, as a hat, would be about as stable and secure as the nation itself.

They debated, argued, and insulted each other for three months, before finally coming down to two finalists.

North Unsteadistan was united in favor of my Gatsby Fedora. Good choice.

South Unsteadistan was equally in favor of my Keeneland. Equally good choice.

Three separate duels were fought over the issue. Two men and a woman lost their lives. A rare albino camel, frightened by the gunfire, ran off into the desert and was never seen again.

Citizens of both nations mourned the loss of the camel.

No agreement was reached regarding an official national hat. They did agree to call Marcie Polo.

She flew in on a chartered DC3 that looked as if it had just flown out of an old movie. She insisted on riding a camel from the airport to the conference center, to express solidarity with the runaway albino camel.

You can always count on Marcie for great photo ops. And a round of drinks. The press love her. As do the-– well, let’s not bring that up just now.

Marcie met with both sides. She asked for a couple of days to study the issue.

She studied by the hotel pool. Often consulting with Piña Coladas and Mojitos. Constantly on the laptop, researching hats, both nations, and peace treaties of the past century. While also squeezing in a little power reading of Sun Tzu, Niccoló Machiavelli, Henry Clay, and Gandhi. She told me she did not look to Gandhi for any fashion advice. (You have not heard True Magical Laughter until you have heard Marcie Polo laugh at one of her own jokes.)

About the time her bar bill hit four figures, Marcie saw a simple solution. Compromise. Channel Henry Clay. A little of this, a little of that. A little from one side, a little from the other side. Time for another Great Compromise.

Combine the two styles.

And order more drinks.

Gatsby crown. Keeneland brim. Brilliant. A nation with both style and attitude. Mission accomplished.

Unanimously approved.

Well, not quite. We still need your vote.

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