Charlie asks: I’m getting close to the end of my grad school years and am looking to hang up my backpack for good and replace it with a briefcase. We always match our belts and shoes, but what about leather bags? Is matching one’s shoes with one’s bag something best left for the ladies?
Generally speaking, don’t worry about it. The above photo (by the Sartorialist) is a great example of a man whose case does not match his shoes, but nonetheless looks great.
The briefcase basics largely breakdown along serious/less serious lines: black is a little more serious than brown. Hard is a little more serious than soft. A refined aesthetic is a little more serious than a rough one. Bear in mind, though, that these are for the most part fine distinctions.
Matching bag to shoes can be nice, but few people want to take everything out of their briefcases in the morning to match them to their choice of footwear. My recommendation is to consider the color shoe you’ll most frequently wear, and buy a case in that color. If you’re a brown casual shoe type guy, maybe a black hard case isn’t the choice for you. If you’re a sober banker, perhaps a floppy brown bag won’t fit your style. You can also consider a color like burgundy, which will relieve you of the pressure to match almost completely.
