I’ve paid attention to stylish clothing since my first job at K-Bliss Men’s Store in Menomonie when I was 16 and took a job arranged by my high school’s distributive education class. I learned from three experienced associates how to match a tie to a dress shirt, how to measure pant legs for tailoring, how to choose the correct size for suits and sport coats, and how to casually suggest accessories like cufflinks, cologne, a second tie, a new belt, or a pocket square.

I enjoyed the job and discovered the sales tactics they taught worked, and I became a good men’s clothing salesman. From the time of that job in high school, I paid some attention to my clothing style and occasionally read men’s fashion magazines at the library.

Many years later, my stylistic sensibilities were piqued when a friend commented about my motorcycle. “Greg, I’ve noticed that bikes are a lot like their owners,” I asked what she meant. “Your bike is sharp, clean, smart like you.” Her compliment charged my ego, and I began studying motorcycle and rider combinations. I realized her observation was accurate.

With an enthusiasm for motorcycling and voguish dress, it’s no surprise that I felt drawn to The Distinguished Gentlemen’s Ride (DGR), a motorcycle charity and awareness event with an eye on riding dapper. The DGR was founded in 2012 by Mark Hawwa in Sydney, Australia and has taken place around the world every year since then. Hawwa prefers not to take credit for the ride’s success but turns the focus back to its mission.

The DGR is unique in its focus on smaller, classic motorcycles. The riders dress in snappy clothing to evoke an era when life was decelerated and not defined by horsepower, back when courteous riders traversed the roads wearing bow ties, suspenders, tweed coats, and manicured boots. The DGR is about motorcycling and fundraising, but it also takes style seriously and includes a “dapper guide,” on its website to advise riders how to dress as a way of embracing nostalgia for the day when sharp-dressed men rode street motorcycles with civility, courtesy, and engaged brains.

The worldwide ride has grown more inclusive over the years, so that classically dressed women are included both as drivers and pillion riders. The event is officially known as The Distinguished Gentlemen’s Ride, but communication to riders uses the broadly welcoming “Gentlefolk.”

The DGR is a financial boon for prostate cancer research and men’s health. Not including the 2025 numbers, 500,000 gentlefolk in 121 countries have ridden in the Distinguished Gentlemen’s Ride. This year, the Distinguished Gentlemen’s Ride was held on May 18. Since the ride’s inception, over USD 50 million has been raised for men’s health research and treatment.

The DGR has also created incentive-based ride contests with awards to winners. In 2020, organizers held a worldwide photo contest for riders to show their bikes and riding outfits. The top 10 entrants for haute couture, matched with a classic motorcycle, were promised prizes. For the fun of it, I dressed up in my dapper ride suit next to my bike and entered the contest. I ride a Royal Enfield Classic 500 to which I’ve made a few cosmetic modifications.

After the 2020 ride, I heard nothing about my photo entry. As time passed, I forgot about the contest until the day a high-fashion magazine from England arrived in my mailbox. I hadn’t ordered it but enjoyed the magazine and wondered when my bill would arrive. No bill arrived, and I thought the magazine was a one-time mistake. Three months later, when a second quarterly issue of The Rake showed up at my door, its mission statement caught my eye. “Elevate your wardrobe with premium menswear from The Rake Store in Newcastle, the modern voice of classic elegance and the champion of discreet luxury.”

It dawned on me that the magazine may have something to do with the DGR photo contest, so I perused the DGR website and discovered that my bike and I had placed 10^th in the worldwide contest, and that’s why I was receiving the magazine. The first three winners received expensive watches, the next two received other prizes, and the last five winners received the magazine only. It is a good magazine, but honestly, the price for its advertised clothing, watches, suits, ties, shoes, and accessories are out of my league.

I saw that the first-place winner was an International Financier living and working in the United Arab Emirates, and by his social media, I can guess he’s loaded. His elegant dress on Instagram shows him wearing the throbe, or dishdasha, complemented by expansive accessories. His self-appointed handle is, “World’s First Cigar Sommelier.”

I ended up on that list with Mohammad, the winner, not because although I operate with fistfuls of dollars, but because I know how to scramble and make something from nothing; I know how to dress, and how to present my motorcycle as part and parcel of what I am, a dapper DGR rider.

WHY I RIDE?

Friends of mine have died from prostate cancer. Friends and family have died as a result of suicide. These two major issues are the big reason I ride. A third reason is that I, too, have had prostate cancer. I was lucky, mine was detected early; nevertheless, I had radiation treatments, and I am monitored by my doctor. So this ride is not just about fun and dressing up for me, it’s also about supporting and remembering the reason that thousands of people from around the world are riding on the same day. We support research and treatment for men’s health issues. I also ride and support efforts on women’s breast cancer and MDA.

My link for DGR fundraising.

https://www.gentlemansride.com/fundraiser/GregoryOrmson288222