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What A Gentleman's Hat Says About His Romantic Intentions

For there is nothing more fedorable than a courting man in a handsome cap.

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The Protégé

Danny Moloshok / Reuters

"There is none more comfortable in his sexuality than I, as evidenced by my hat equally at home on Mick Jagger, Carly Simon, and your local Amish merchant. The wide brim of my hat signifies the breadth of my open mind. Join me?"

The English Crown

Kris Connor / Getty Images

"Long before the fedora's name was sullied by the colonists, it was the chosen chapeau of the British isles. But let us speak no more of these orbital ornaments, I'd rather take you for a drink and a laugh."

The Skyfall

Marko Volkmar/iStockphoto

"Our love shall soar to great heights but be a greater aviation tragedy than that of Amelia Earhart because of my philandering ways. You deserve better than me, even though the world conspires to tell you otherwise."

The Chuckling Beerman

"My willingness to wear a silly costume is actually indicative of whimsy and the desire to make a woman laugh. Come, let's have an unforgettable romp."


The Jester of Oakland

" 'A' is for absolutely ready to party, milady! With me, you shall feast not only upon cupcakes but on my infectious joie de vivre!"

The Home on the Range

"I'm my best self out on the range, but my range of romantic interests starts and ends with you, little lady."

The Scholar's Regret

"Before I was crushed by the heavy crown of higher education completion, I was different. Gentle. Hopeful. Tender. The burden of my achievement shall wreak havoc on my priorities and I'll never love a woman like I could before this cranial shackle."

The Mulder

Matt/Scherf / Getty Images

"The truth is out there, but the questions remains in my heart: Will I find true love on this tender blue planet I call home? Will you? These questions are probing, to be sure, but I want to believe we can answer them together."


The Scottish Heist

Getty Images

"I have the courage to rob a Scottish soldier of his prized uniform cap; to steal your heart will be no trouble. I enjoy hiking, sunsets, and have a surprising penchant for fruity cocktails. Sex on the Beach, my darling?"

The Madman at Dusk

Danny Moloshok / Reuters

"I do not fear a bold and inscrutable fashion statement just as I don't fear a bold and inscrutable woman. Though my sartorial choices are a mystery, you will know the truths of my heart if you gaze deeply enough."

The Canterbury Male

Hemera Aleksandar Todorovic / Getty Images

"My daytime commitment to live-action roleplaying has made me an open-minded expert in all manner of nighttime shenanigans and a sucker for a chivalrous deed."


The Stoner's Arc

"Being high all the time might seem at first blush a drawback, but do trust that it enhances my sexual longevity. My expectations are not exclusively carnal, but when I have a carnal desire, I have it exclusively for one lady."

The Last Mate

"The same fiery passions that draw me to whirlwind romances are also what draw me to the high seas. I will lose myself in the deep ocean of your eyes but may also be lost in the literal depths when I embark on maritime adventures."

The O'Keefe

"I may disguise my general ennui with bold, brightly patterned hats but I will never disguise my affections for you. I'm a good listener and an even better cuddler!"


The Scoundrel of Panama

Alberto Pizzoli/AFP / Getty Images

"I do confess to keeping undisclosed sums of oil wealth but I will never keep my feelings for you undisclosed. I'm a man of my word in love and in lust, if not always with the federal government."

The Way of the Future

Sean Gallup / Getty Images for Sony Pictures

"Hush, dear maiden. I come bearing no hat, only a monocle, crafted in Hell. I can read your thoughts and I wish for you to know that no harm will come to you in my arms, nor in the embrace of my ghoulish ocular ornament. Shall we dance?"