Book of Daze

Observe National Side Saddle Day, Enrage a Feminist℠

Today is National Side Saddle Day, that noble observance in which we honor the brave riders—almost exclusively women—who once believed that dignity, modesty, and personal safety could all coexist on the back of a moving horse. History would later clarify: it could not.

Side saddle, for the uninitiated, is the riding style in which a woman perches sideways atop a horse, hands gripping the reins, feet arranged like a folded lawn chair, knees functioning as the world’s first seat belt. The idea was that this allowed a lady to ride without straddling the horse, thus preserving propriety, posture, and any chance of walking comfortably afterward.

The practice reached its cultural peak during the era when long skirts, high collars, and fainting couches roamed the Earth. Aristocrats promoted the technique as “perfectly safe,” which was true provided that the horse did not move, breathe, or think independently. In actual use, however, side-saddle riders often found themselves slipping, dangling, or performing involuntary cartwheels into the shrubbery—activities collectively known as “Edwardian Pilates.”

Today’s holiday encourages the rest of us to appreciate the grit of those early riders. Imagine maintaining elegance while riding sideways at a trot, adjusting your hat, avoiding tree branches, and desperately hoping your mount didn’t have opinions about anything. These riders were the original multitaskers, the forerunners of modern commuters who apply makeup in traffic or hold conference calls during dental cleanings.

Modern equestrians occasionally attempt side saddle for sport, spectacle, or the thrill of tempting gravity, but it remains a historical curiosity—an elegant solution to a problem nobody has anymore.

So raise a toast to the side-saddle pioneers. They sat tall, they rode sideways, and they reminded us that fashion has always demanded sacrifice—especially from anyone unlucky enough to ride it into battle.

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The preceding is satire. Straight up, Skippy. No warranties are expressed or implied. For life advice, try a professional. For investment tips, try a dart board. For salvation, the gentleman in the robe has been handling that portfolio for 2,000 years.