Hey gents —
Let’s keep this short and sweet. Cognac-colored leather is vibrant and eye-catching. It looks great with a range of different outfits, as suggested by the image above. Get them in a brogue (see the Florsheim above in more detail here) or a cap toe (Florsheim’s Canfield is a good option, seen here) and you’re set.
So, what do you wear with these exactly? For starters, a dark gray or navy suit is always a safe bet. Match the socks to the suit, or go for contrast and find striped socks with colors complementary to the cognac (such as these, these, or these… all from Paul Smith.) Keep the vibe dressy while remaining casual by pairing them with dark, raw denim. Keep the whole thing balanced with a lighter-colored button down and a heather gray sweater, gray sport coat, or tan plaid jacket. Go the dapper lumberjack route and wear them with a heavy red flannel jacket and distressed mid-wash denim, or ditch the flannel and throw on a navy pea coat over a golden or maroon merino wool v-neck sweater. Happen to have a plum- or tomato-colored merino or cashmere sweater? More power to ya.
Bottom line is this: It’s difficult listing specific head-to-toe wardrobe choices for this shoe (or any shoe, which you will soon learn) because there are numerous color and texture combinations, and one can only become awesome at correctly combining them through experimentation. Use the above pointers as a general guideline on how to incorporate these shoes into your everyday wardrobe. As with any rule or guideline, however, there are exceptions and any well-dressed man can tell you the rules of style are set in place only to be broken… but do this sparingly and with large amounts of confidence.