A couple years ago, my friend and I went on our first winter backpacking trip. I never buy single-purpose shoes, so when I started looking for shoes for this, I considered only shoes I could use on the daily as well.
What I found were some great Adidas Terrex GTX trail running shoes. They utilize Gore-Tex, so they're completely waterproof, and they're a mid-top, so I won't be wearing boots. Being a year-round cyclist, this was a dream come true! So my first winter backpacking trip went down without a hitch – even though I didn't have high-top shoes, I didn't get any snow in my shoes. While my buddy was drying his shoes out by the fire, I was sitting warm and dry.
I've worn these shoes every day through two Autumns and Winters here in Seattle for cycling and for normal wearing. I've even worn them into the summer until it becomes too warm. I'm wearing them right now, and they're still mostly waterproof. I'm sure I could do something to fix the one part that isn't (right foot, small toe area). But Gore-Tex carries a lifetime warranty on all of their products, so I might just take them up on that.
I paid $70 for these shoes on Amazon, because they were a yester-year model.
This summer, that same friend was having his "bachelor party" trip, where we got a cabin and floated a river. I knew I needed water shoes, but I didn't want just water shoes. I wanted something I could wear like a normal shoe during the summer, since I didn't have any shoes that weren't too warm for the summer. Adidas came to the rescue again with their Terrex CC boat shoe. It's mesh and has holes in the bottom to allow the water to drain out. It was a good thing I got more shoe-like water shoes instead of the barely-there ones, because the river was low, and my feet met some rocks. No harm done thanks to those shoes! I went on to wear them the rest of the summer with and without socks. Those shoes were $52 from Moosejaw.com, and I'll get 10% back in dividends. :)