One of my favorite jobs as a luxury shopping editor is testing out some of the most divisive and head-scratching trends. Mesh shoes? Love. Jeans that are actually sweatpants? Obsessed. Capri pants?

I wear my Weejuns every chance I get ... G.H. Bass has been around for over 150 years, churning out comfortable, stylish shoes (and other goodies) the whole time. Among heritage brands, it ...