I choose my outdoor gear the same way I run IT projects - first I define requirements, then I write specifications, then I choose the right solution for the task to be done.
My 5 Summer activities are
*Walking with my wife in the mornings
*Kayaking the Charles in the late afternoons/evenings
*Cycling Dover/Sherborn/South Natick on weekends
*Hiking the Franconia/Kinsman/Presidential ranges in the White Mountains in Friday mornings. Instead of taking my customary last week of July vacation this year, I'm taking off Friday mornings in July to hike. Given all the Stimulus-related Healthcare IT activity in Washington and Massachusetts, it's easier for me to be available at least a portion of each day to ensure that I'm not a rate limiting step.
*Climbing in New Hampshire and Yosemite
I try to own and carry the most minimal gear possible for each activity. I want to be safe, capable of self-rescue, and reasonably comfortable, but I always want to be light and fast. In many activities, an agile response to changes in weather is safer than carrying a heavy load of equipment.
Each of my activities requires specialized footwear and I have selected shoes that meet my requirements, providing optimal function without a lot of complexity.
For Cycling, I use Pearl Izumi X-Alp Seek, a lightweight riding and running shoe that enables me ride on or off road, hike to my final destination, and portage my bike through mud/water.
For Hiking, I use the Five Ten Savant, an amphibious shoe what enables me to hike through rain, mud, river crossings, swamps, and canyons without worrying about getting my feet wet. The Savant drains so well that I arrive at my destination with dry and comfortable feet.
For Climbing, I use the Five Ten Prism that are optimally shaped for edging on small footholds and crack climbing.
For light treking/walking, I've used the Chaco Unaweep Z1 but their heavy sole is really more than I need for flat trails. For Kayaking, I've used NRS Kickers neoprene booties but they are really too hot for summer and neoprene really smells bad in warm, humid weather.
So, I needed a lightweight protective shoe that meets my light hiking and warm weather kayaking needs. My search led me to Vibram KSO Five Fingers. My daughter describes them as the strangest looking shoes she's every seen. Although they are indeed different than other footwear, they are light, durable, comfortable, and ideally suited for light trails and kayaking. Wearing Five Fingers feels like walking barefoot but without damaging your skin on rocks and roots. They dry rapidly, and their low volume means they are easy to fit into tight kayak hulls or narrow surfski footbraces. I would not have predicted that Five Fingers would work so well, but they are my favorite outdoor shoe at this point. Of course, I'm not likely to win any fashion awards, but I'm an engineer, so judge me for my efficiency, not my sense of style.
Since my feet are ultrawide (9EEE), I usually buy a half size larger shoe (9.5). However, the standard sizes of Five Fingers work perfectly for a wide foot. Check out the Vibram Five Fingers - together we'll make it a trend.