Teddy and the True Panama Hat

By Mallory Passuite

The history behind your grandfather's hand-me-down wardrobe staple

Few trends have dressed as many prominent people as the Panama hat. It links the wardrobes of Ernest Hemingway, Hannibal Lector, and Madonna. Winston Churchill, FDR, and a young Obama all wore one. Today we’ve seen the classic (and practical), light, woven-straw, black-banded hat on everyone from Sean Connery to Mischa Barton to Yoko Ono.

But much of the Panamas’ true saga remains hidden beneath the brim of this legendary hat. Its name a misnomer – the original Panama hat is hand-woven in Ecuador, dating back to the 1600s and is made from the Ecuadorian coast’s native Toquilla plant. It takes anywhere from a day to several months to weave a single hat, depending on the quality of the Toquilla straw, the weave, and the skill of the weaver.

Before the 20th century, the hats were exported and sold internationally from Panama, a great trading center at the time (and part cause of the misnomer). Hats left Panamanian markets to grace the heads of European royalty, including Napolean Bonaparte and King Edward VII of England. In the same markets, the US government bought 50,000 hats for American troops to wear while fighting in the Spanish-American war.

The hat’s improper name spread after 1903, when President Teddy Roosevelt became the first president to visit the Panama Canal, and the first American president to visit a foreign country. There, Teddy saw workers building the canal, all in the same light hat so he put one on too. A news photograph of Teddy wearing his new hat in Panama circulated in America, extending the revere (and false name) of the Panama hat across the US.

And it’s been a summer staple ever since.

Buying Tips:

- If you’re looking for an authentic, real deal “Panama” hat, make sure the label reads, “made in Ecuador.” While most come from the Ecuadorian town, Cuenca, Montecristi is known for finest-quality (and most expensive) hats. A Montecristi can cost around $1,500 but you can find an authentic version for under $40.

- If you can avoid buying online, always try it on before you buy. Each hand-woven hat will look and fit slightly different. Panama hats come in a variety of shapes, but even hats of the same shape will vary (whether the brim is slightly wider, or curved more upward in the front) – it makes a difference.

J Crew currently carries an authentic line of Panama hats in tan and white with the classic black ribbon for $58. But if you want the look, want to spend less, and don’t care about authenticity, Urban Outfitters offers a selection for under $30.

Slideshow produced by Mallory Passuite

Mallory Passuite is a regular contributor to Jerk Wear.