My favorite boots of all time are my Vasque Sundowner hiking boots. I bought my first pair back in the mid 1990s and wore them on the trail in all conditions and loved the support the provided. I also wore my Sundowner boots with jeans and Khaki pants as they looked great when cleaned up. The Gore-Tex insides kept my feet from overheating and the leather kept my feet secure and dry. I would wear a pair of Thorlo hiking socks and dominate with comfort.
At $200 bucks they were expensive boots. As I was a struggling college student this was a huge investment, but one I made after a lot of research. I bought my second pair of Sundowner hiking boots a few years ago and had to search to find them. The style had changed so I bought what was labeled as “Sundowner Classics.” They are great boots too, but will never hold the place in my heart that my first pair held. I guess your first pair of great hiking boots is like owning your first car.