Including gear? My Brooks Ghost sneakers for walking the dog in warmer months and the treadmill (one pair for each activity, so I don't wear down the tread too fast), and my LL Bean duck boots, North Face lace-up boots, and Ugg boots for walking the dog in colder months (in wet, cold, and really cold/snowy conditions, respectively). We walk our dog 3x/day (.5 to 2 miles/walk) in all weather, so I finally invested in a bunch of different footwear to keep my feet happy all year!
Not including gear, I would say a pair of black Troentorp clogs this summer, but once it cools off it will likely be a pair of boots! Clogs are comfortable and I like how versatile they are; boots and booties are my favorite footwear--comfy, versatile, durable, rugged, really suit my style.