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.

The Classic Fedora in the top three photos is size 71⁄4. Crown is 41⁄2 inches tall. Brim is 23⁄4 inches wide. $650.

Look at that weave! This is the same Classic Fedora style shown above. But I had these hats custom woven for me with specially designed “open weave” crowns.

The dark areas are spaces between the straw. The light areas are the straw itself. This style of “open weave” allows the trade winds to have free trade with your head. Sort of like having an air conditioned hat, hence the (AC).

I have a personal hat with this diagonal pattern. It’s one of my favorites. I like it so much I thought you probably would too. So last year I decided to commission a few dozen hat bodies to be specially woven for me, all with this same pattern.

Usually, the geometric designs in the weave change from hat to hat. None of the weavers could remember anyone ever making several dozen hats with the same geometric pattern.

Get ’em while they last.

The Classic Fedora (Special AC) in the photos is size 71⁄2. Crown is 41⁄2 inches tall. Brim is 23⁄4 inches wide. Ribbon is 11⁄2 inches wide. $500.

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.

The Gatsby in the top two photos is size 73⁄8. Crown is 43⁄4 inches tall. Brim is 27⁄8 inches wide. $1000.

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 71⁄4 and 73⁄8. The ribbon is Jamaica 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

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: Roll-Up 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.

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.

The hat in the photos is size 7, crown 41⁄4 inches, brim 23⁄4 inches, ribbon black grosgrain 11⁄16 inch, $650.

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.

The hat in the top three photos is size 71⁄4, crown 5 inches, brim 27⁄8 inches, ribbon black grosgrain 11⁄2 inches wide, $650.

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.

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.

Good idea, Trent. I think you’ve created an instant classic.

The front of the brim looks flat, instead of rounded in these photos. I don’t know why. The brim edge is round all around. Optical illusion. I’ll fire the photographer. Wait, can’t do that. I’m the photographer.

If cowboys wore Panama hats, this might be the style. The Western brim dips down front and back, lifts up like wings on the sides.

The first time I wore this style in public I was chased into the parking lot by a bartender at one of my town’s better beach front restaurants. He had seen me going out the door and wanted to know where I got the totally maxin’ hat.

I handed him my business card and told him to go back inside and get his attorney. I figured there was a much better chance his attorney could afford the hat.

This is the same crown block as the Plantation, Aficionado, and Classic Fedora. The brim style is the difference. This brim is shaped on flanges that were found in an old building in Colorado in an attic that had been sealed up for more than a century.

Isn’t that great? After more than a hundred years of being forgotten and useless, seven old Western hat brim flanges from the nineteenth century have purpose again in the twenty-first. I like that.

People sometimes accuse me of trying to set the hat industry back a hundred years. Not really. Just my little part of it.

As for the style, it’s a keeper. The hat in the photos is my personal hat.

It’s definitely a Western hat. The brim defines it. Western. You can probably wear this hat successfully anywhere between Westchester County and West LA, including authentic Western states where people still know a lot about hats. The brim shape is the real deal and the crown looks so darn good someone will probably try to buy it right off your head the first week you wear it.

When I said anywhere between Westchester County and West LA, I meant if you go the short way. If you go east from Westchester County or west from West LA, you’re on your own.

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. In the top photo the brim is about 31⁄8 inches with a slightly larger than regular curl. The same hat is shown in profile. The Monte Carlo in the second photo from the top has a wider brim and a regular curl. The same hat is shown in the bottom photo.

Brim width can vary from about 23⁄4 inches to 31⁄2 (after the curl). Curl diameter can vary from about 1⁄4 inch to about an inch. Send me an email or call if you want help deciding.

Before the Tiger leapt onto the course, the Shark was at the top of the food chain on the links, and at the top of the sales charts for golf hats.

His golf hats were exactly that—hats. Hats with brims all the way around. Sun protection for the back of your neck and the tops of your ears. That is a very good thing. How did everyone forget that?

Golfers also enjoyed the advantages of an open weave, or ventilated, crown. The breeze blows right on through to keep you cool-headed at all times (not an easy task when you’re putting for a birdie on the 18th at Augusta).

But now, alas, golf caps are the trendy choice of millions, and you know what that means: the world’s golf courses are filled with a bunch of hot heads with sunburned ears. Perhaps it’s time to elevate your game by elevating your choice of headwear.

I suggest the Golf of Panama, also known as the Monte Carlo (AC). Monte Carlo is the style name (same style as this one) and the AC stands for Air Conditioned, to signify the open weave, patterned crown. This is not just a hat, it’s Art. The artists of Montecristi weave the straw of the crowns 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.

Woven by hand in the Montecristi area. Blocked and finished by hand in Hawaii. Black grosgrain ribbon outside. CoolMax® sweat-wicking band inside. Leather sweatbands also available by request. The wide brim offers sun protection. The open weave crown provides natural air conditioning.

Some clients swear that the Monte Carlo (AC), aka The Golf of Panama, takes at least five strokes off their game. I’m inclined to believe them.

Mombasa. I’ve always loved that word. It sounds so exotic, distant, dangerous. Mombasa is, of course, a port city on the coast of Kenya. If you were going on safari in East Africa a hundred years ago, Mombasa might have been where you got off the boat and began your journey into The Dark Continent.

You would have wanted a good sturdy hat to shade you from the Equatorial sun. A hat that would also look quite dashing in the flickering light of the evening cookfire.

The Mombasa would have been a perfect choice. For both you and the Memsahib. Classic center dent crown. Safari brim (3–31⁄4 in). Black ribbon (11⁄2 in). Choice of fine leather, cotton twill or CoolMax® sweatband.

Should you be a sensible soul who prefers to skip the safari part and explore the shaded veranda and libations at the Lodge instead, start with a Tusker beer, well chilled.

The Mombasa can be a good travel hat, but it is not a roll-up hat.

GUARANTEED AGAINST
ELEPHANT TRAMPLING

A Montecristi hat is so tough that I guarantee this hat will even stand up to being trampled by an elephant. The nice blocked shape will be history, of course, but the hat itself will survive a good trampling far better than you would.

Return the hat along with photos and/or video of the trampling event and I will replace your hat. The better the camera work, the more cheerfully I will make your replacement.

The Mombasa in the photos is a Safari grade with cloth band. Size 71⁄8, crown 43⁄4 inches, brim 31⁄2 inches, ribbon black grosgrain 11⁄2 inches wide, $525. In the first through third photos, the brim has a slightly different shape than the same hat in the fourth and fifth photos.

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.

The hat in the top three photos is size 71⁄8, crown 41⁄4 in., brim 3 inches after the medium sized curl, 31⁄4 inches uncurled, $700.

Bottom hat is a Greenstreet (AC).

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.

The hat in these photos is size 73⁄8, crown 33⁄4 inches, brim 27⁄8 inches curled, 31⁄4 inches before curl, $850.

Also known as The Homburg. This hat was made as a special request for a client who’s a financial whiz by day and a blues player by night. He was so happy with his hat I fear his blues may suffer. He thought the style should be called the Big Daddy. Works for me.

This is a tall hat with a short brim and an extra-wide ribbon. A very dressy style. Or a very hip style for those who have enough style of their own to make it work.

Deion Sanders could own this style. I can easily imagine this style on musicians. Jazz, salsa, hip hop, rap. Not a lot of accordion players.

Wear this hat into an interesting bar and others will buy your drinks just to find out what’s up with the hat.

I first saw a Panama hat homburg on George Kennedy in Death on the Nile. His hat just knocked me out. I remember playing that scene over and over and pausing several times so I could study the hat. Peter Ustinov wore a Panama hat homburg in Evil Under the Sun. Kennedy’s had a crisper look. As did his character.

After I finished the first Big Daddy, I immediately started another one. For myself. That’s it with the brown ribbon.

The hat bodies I use for this style are specially woven to have taller crowns. I used some of these taller hat bodies to make Montecristi Top Hats. (I still have a couple around here somewhere.)

The hat in the bottom photo is size 71⁄4, crown 5 inches, brim 21⁄2 inches, ribbon Havana Brown grosgrain 2 inches wide, $1000.

A Derby. A Montecristi Derby. I just couldn’t resist. The hat in the photo is a personal hat.

I have a lot of shirts with old fashioned stand up collars. The Derby is very right with those shirts. Vertical stripes are nice. Maybe a vest. A silver-handled walking stick might be fun.

Another way to go with the Derby would be dressed-to-the-nines formal. If you attend the Kentucky Derby, wearing my Derby might be a good way to get on TV when they feature great hats. (Just for the record, I grew up in Kentucky and this is the hat I wore last Derby Day while mixing family recipe mint juleps. Served in Kentucky-made sterling julep cups, of course. Even here in Hawaii, I still celebrate the first Saturday in May as Spring’s High Holy Day.)

You could wear a Derby to a polo match. It would look good with a cigar in your mouth and your elbows on an old mahogany bar (works for men or women). Wear one around London in the summer and sooner or later someone will offer to buy it right off your head. Take several. Pay for the trip.

The hat in the photos is size 71⁄8, crown 43⁄4 inches, brim 21⁄8 inches after curl, 21⁄2 inches uncurled, $850.

The Downing Street is very similar to the Big Daddy. The difference is the pinches. One simple difference creates a completely different look.

This is another attitude hat. If you could wear spats to the club and make everyone else wish they had some too, then you’ll be fine.

If you decide to wear the spats and the Downing Street, give me a call. I might like to come see that.

Hat in photos is size 71⁄8, crown 41⁄4 inches, brim 25⁄8 inches, ribbon 11⁄16 inch black grosgrain, $750.