I was on vacation stateside in Portland, Oregon enjoying the Pacific Northwest’s beauty, character, people, and—of course—machines. The summer’s agreeable weather persisted with autumn knocking on the door. Days were warm. Nights were cold. Winds were crisp with layering permitted. DGR was scheduled for September 25—where riders were invited to take out classic and custom motorcycles in their most dapper attire through their respective cities all over the world.

The dapper gentlemen and their motorcycles

The Distinguished Gentleman’s Ride was birthed in 2012 by Mark Hawwa in Sydney, Australia. “It was inspired by a photo of Mad Men’s Don Draper astride a classic bike and wearing his finest suit. Mark decided a themed ride would be a great way to combat the often-negative stereotype of men on motorcycles, whilst connecting niche motorcycle communities together,” says the official website.

More importantly, DGR is about raising money and awareness for men’s health with a concentration on prostate cancer. What started out as a fun way to unapologetically express one’s metrosexuality pivoted towards a greater cause for its second installment and beyond. Every year more cities and motorcyclists join DGR, collectively contributing millions of dollars to prostate cancer research.

Movember movement with The Gentleman's Ride

This year, because of the loss of a DGR ride host to depression, the event also partnered with The Movember Foundation. In conjunction with fighting prostate cancer, DGR 2016 pledged additional support to suicide prevention programs as well.

It was my second time shooting the Distinguished Gentleman’s Ride in Portland. Early that morning, I made it to the traditional meeting place at See See Motor Coffee Co., a local cafe and biker shop for those of the retro persuasion. Its surrounding streets were already populated with parked motorcycles while folks steadily rolled in, clad in their Sunday’s best. It was a flurry of suits and ties, tweed and waistcoats, colorful socks, dress shoes, and vintage styled helmets. Everyone looked good and knew it. A bent knee in slacks revealed reinforced riding boots. The shape of protective armor pushed out from underneath well fitted jeans. The fearless wore kilts.

One of the gentleman riders giving a thumbs up

The route took the participants around the ‘City of Roses’. They crossed several bridges to all four quadrants, making the ride more complex and much longer than last year’s. Some people got separated and some got lost; I suspect traffic lights played a role in that. The destination, however, was clear: Portland International Raceway. All congregated there, where a motorcycle race and autocross session were going on.

“It was funny. I noticed all the pedestrians waving and smiling with their cellphones out were women, while the guys they were with just stood there,” A perceptive rider laughed. After the usual hobbyist chitchat typical for a meet, eventually the crowd thinned and it was time to go. Many wanted to take advantage of the beautiful day to keep on riding, and I needed to make my way back to town.

Ready for the road

The personal builds were perfect conversation pieces (the custom Buell XB12R was insane), a couple of beautiful vintage motorcycles made appearances, and some older models were a very welcome sight. After all, the organizers’ intention has always been to rally “Cafe Racer, Bobber, Classic, Tracker, Scrambler, Old School Chopper, Modern Classic, Sidecar, Classic Scooter, Brat Styled motorcycles,” according to the website.

A gentleman and his Triumph

Does the presence of bikes that don’t fall under those categories muddle things? My observation was that all seemed welcome. A well assembled outfit on a beautifully nostalgic bike makes for a powerfully harmonious image, but the juxtaposition of a suited cavalier on a modern sport bike or tourer is grin-inducing in its own unique way. If you want to dress up for the advocacy, go for it. The more the many-er. Feel the wind, hang out, and enjoy!

It ain’t just about looking good and populating the Instagram or Pinterest accounts of aspirational fashionistas and hipsters. It’s not just about giving photographers material for your next profile pic (although I’m grateful, because God this stuff is fun to shoot). It’s also about celebration, social interaction, health, and hope. Sure it didn’t use to be that way at first, but the organizers decided to turn it into something bigger… And much bigger it has become.