Good pair of handmade American boots. Bought a pair of Chippewa for about $500 several years ago. Aside from the occasional resole, the leather only looks bette

Good pair of handmade American boots. Bought a pair of Chippewa for about $500 several years ago. Aside from the occasional resole, the leather only looks better with age -- and all you need is a good polish and brush to get them ready. You can also dress them up or down, depending on the occasion. In my opinion, shoes are some of the few things you should splurge on -- but do look at build quality, and not just a brand name. For example, some of the higher end Timberlands will run you about $250-$350. Despite the high-price they are cheaply mass-produced in China, and the build quality reflects that.