Island Shop: The Caribbean’s Most Expensive Panama Hat


Above: the Caribbean’s most expensive Panama hat at Olé (All photos by CJ)

By Sarah Greaves-Gabbadon
CJ Travel Editor

Would you pay $3,000 for this Panama hat (above)?

Chances are someone will.

After all, the most expensive hat ever sold by Olé, the milliner, craft and souvenir store here in Old San Juan, Puerto Rico, had a price tag of a whopping 6,000 bucks. And it was purchased, I’m told, by none other than the Prince of Morocco. By comparison, the $3,000 versions (there are two, kept in a locked glass case) seem like a steal!

So what makes a hat worth thousands of dollars? Oriana, Olé’s manager of 25 years, tells me that you can judge a Panama’s quality by the closeness of the weave.


The best are made entirely by hand and are so tightly woven that when you hold them up to the light, none permeates the straw.

And the hat’s “hand” (feel) is much closer to that of a fine fabric than of the rugged texture usually associated with fiber.

Pricey Panamas are flexible enough to retain their shape after being folded or rolled, and are guaranteed to set you apart from the baseball cap-wearing masses.

Convinced but coming up short on funds?

Fortunately, Ole’s inventory of 5,000 Panama (and other styles) of toppers starts at $60, so they won’t completely demolish your souvenir budget.


Pick the one you like and then customize it with the colored ribbon of your choice. And once you get it home, make sure to keep it in a humid spot such as a bathroom (or mist with water periodically) to prevent it becoming too dry. That way it’ll last you a lifetime. And your prized Panama will end up costing mere pennies a day.


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