Double-H ICE™ Old Town Folklore Buckaroo Boots DH5159
A combination of three insole technologies make this one of the most comfortable boots, it has the Ultra-Welt insole (with Gel Cell in the forefoot), removable DRYZ footbed and Gel Cell Insert Heel. The Oak ICE outsole, which is one of the most durable outsoles, will let you wear these babies for a long time.
Not to mention, the classic style with the leather interior and exterior, subtle stitching and round toe will stay relevant for many years.