Tan shoes can be tricky to wear, especially during the colder months. Most men rely on dark jackets with lighter-colored trousers and dark shoes, so inverting that combination can feel unnatural. Tan shoes can be easier to pull off in the spring and summer seasons, when everything we wear naturally becomes a bit brighter, but for the brown tweeds and grey flannel trousers most of us rely on for fall and winter, darker colored footwear is almost always a better choice.
There are exceptions though. If you want to add a little variety to your wardrobe, try a pair of traditional country shoes, such as hefty, double-soled boots or Norwegian split toes. In tan suede or pebble grain leather, they go great with brown moleskin trousers, lighter-colored jackets, and light-blue shirts. The textures and patterns in the picture above, for example, keep things autumnal, while the color combination is a bit more interesting than your usual mix of dark browns, grays, and navy blues. You can also wear tan shoes with khaki or olive chinos and a mid-brown sport coat, or some jeans and a causal jacket.
The only caveat when searching for the right pair: watch out for tans that are either too bright or have red undertones. Those that are subdued and have earthy, cooler yellows and greens at their base are often easier to wear, especially if most of your wardrobe also relies on cool colors (e.g. an earthier tweed, rather than a warm, reddish tweed). Edward Green’s burnt pine is an example of a good, versatile tan, while Allen Edmond’s walnut can be tougher to pull off. For a versatile tan that’s (relatively) affordable, look into Loake’s 1880 line. I dig these pebble grained chukkas.