Good boots are what makes being out in nature comfortable. Well, they are one of the things, but they are also the big thing.
Shoes with a Gore-Tex barrier are truly waterproof. Shoes with XCR (Extended Comfort Range, another Gore-Tex product) are merely water-resistant. But my shoes with XCR have never let water in, even while quickly crossing shallow streams. Waterpoof boots don't breath as well as non-waterpoof boots so your socks may have just been wet from sweat, and there's a huge hole on the top of ever single shoe where water can get in.
I've been using Vasques for 10 years now, highly recommended them since they are great boots. As are nubuk leather boots with a rubber seam above the sole and and a gore-tex liner.
The thing to remember about any shoe that is supposed to keep water out is maintanace. Reproofing boots, like with jackets, is really important to keeping the performance up. 3 years of heavy use is the best you can hope for from a pair of boots even with regualr care.