Most people might think that the only time it’s appropriate to wear socks with sandals is, well, never. Usually I’d agree with them on this point, or at least I would have until I began immersing myself in a culture of dirt bags, vagabonds, young hearts and old souls that mostly live in flips flops, Chacos, and/or bare feet. With more miles put on my Chaco flops than I could possibly recall, I’ve personally deposited my fair share of dilapidated flip-flop rubber in some of the most remote places of the world. With that said, I still think the whole socks-with-sandals thing has its time and place, those of which are few and far between. But I have a few ideas of when it may be acceptable to snap the elastic on those fuzzy wool socks while rocking the sandals. Yes, with a robe on and a cup of coffee in hand, you might look like an old fart settling into a life of early retirement, strolling out to get the Sunday paper. But in a few cases, it might just be legit.

Being a “professional” raft guide and living out of a 90-gallon kayak for three months at a time, has offered very few situations where I could take the muck boots with me.  On any adventure, though, I can always make room for a pair of sandals. In the lush mountains and dry desserts of Peru, weather can be—what’s a politically correct term to sum up pissing down rain, plus suffocating humidity, plus blistering heat, plus rivers flooded to terrifying proportions, plus insect attacks that would rival the plague— Inclement? Yes, that’s it. The weather in Peru can be very inclement.

After 72 hours of jostling across the Ecuadorian border and down the Peruvian coastline, four Americans stumbled into Cusco at 11,200 feet. I can’t recall if it was the altitude that made my brain throb, or the three installments of a poorly dubbed Spanish version of Marley & Me that played throughout the long bus ride, but I learned after that trip to never leave home without earplugs.

Soon after arriving in the cobblestoned city, we made way for the Rio Mupacho, a class V mission in more ways than simply whitewater. Our boats were packed for nine days on an unknown river that flowed into a tributary of the Amazon. Cheese, cured meat, and of course, our Chacos.

The first night, the rain began to fall and didn’t stop for four days. During that time, Max wore his socks with his sandals. We all cracked jokes at him for his lack of camp style. His feet stayed warm and, oddly, more dry and less wrinkled than ours. Day five, still unconvinced, the rain stopped falling, and the flesh-eating sand flies arrived. Their cravings: any piece of exposed skin they could find. All of us spent the next four days in that humid hell in long sleeves and pants slapping at our ankles and howling in frustration and pain with each insect mandible that chewed into our dermis. All of us, of course, except for Max. Sitting smugly and looking like a total genius in his socks and sandals, he knew something that we didn’t: sometimes, it’s okay to wear socks with Chacos.