Pressed Shirt, Polished Steel: The Distinguished Gentleman’s Ride

I learned how to dress when I was sixteen while working after school at a men’s clothing store. The sales staff included four men and one woman, and I was there through a high school distributive education program that paid an hourly wage while teaching sales skills.

The owner and senior associates were good mentors. They showed me how to match a tie to a dress shirt, how to measure pant legs for tailoring, how to choose the correct size for a suit or sport coat, and how to convincingly suggest accessories: cufflinks, cologne, a pocket square, perhaps a second tie?

Over time, I carried these lessons into my professional life. My work required me to move between colleges, hospitals, retail spaces, lunch meetings, and people’s homes. I dressed carefully. Not extravagantly. I did not own tailored suits or power clothing, but my shirts were pressed and cleaned, my shoes polished, and my colors were coordinated. Dressing with care felt like a form of readiness, a bit of soul-craft, and my way of entering space respectfully.

My understanding of style deepened again through motorcycling. A friend remarked, “Bikes are a lot like their owners.” I asked what she meant. “Your bike is sharp, clean, well-taken-care-of, like you.” The comment piqued my attention, and I began looking closely at other riders and how they presented themselves and how their machines reflected the people who rode them.

Pressed Shirt, Polished Steel: The Distinguished Gentleman’s Ride

That curiosity led me to discover the Distinguished Gentlemen’s Ride (DGR), a global motorcycle event founded in Australia in 2012, that raises funds for men’s physical and mental health – especially research and treatment of prostate cancer. The ride emphasizes classic motorcycles and period-inspired dress. Riders wear bow ties, suspenders, tweed coats, and polished boots. It’s an effective way to highlight a cause with the deliberate contrast of a slower ride, smaller bikes, retro style, and sharp-dressed men and women riders.

The DGR holds a worldwide photo contest, and one year on a whim, I sent a photo to the contest after putting on my dapper riding gear and posing with my Royal Enfield Classic 500, a modest motorcycle with a lineage that traces back to England, but with its current manufacture in India.

I didn’t expect anything to come of it and forgot about my submission until the day a high-fashion British magazine arrived in my Arizona mailbox months later. It turned out my photo entry had placed tenth worldwide. The top five received watches and cash prizes.

My bike and photo were number 10 on the list, one shared with international financiers and collectors operating on an entirely different economic planet. But I understood something about care, presentation, and how to squeeze the best out of what I have. Style, I realized, is not about wealth. It is about attention.

A ZZ Top song pressed this idea with their song, “Sharp Dressed Man.” The lyrics celebrate sartorial details: clean shirts, new shoes, cufflinks, white gloves. The point is not luxury, it is paying attention to and caring for presence. A man who pays attention to his appearance is signaling something deeper. He respects himself and those he meets.

He may put on a bowler hat, or he may just polish his boots and match his colors before stepping into the world. Either way, attention changes posture and presence. And sometimes, when care becomes visible, something unexpected draws near; maybe it’s a sharp-dressed man on a motorcycle.