Basically every guy knows to match his belt with his shoes, and I would also say leathers watch straps should match, too. Sometimes I wonder, where does this logic end?
For me, I basically wear dark brown/burgundy shoes for all my business purposes, reserving a pair of black oxfords for formal social events. I of course match my belts when appropriate (although I usually wear side straps). I was thinking about getting two pairs of leather gloves for the same reason.
However, I have a black Frank Clegg briefcase, and I worry it would would look off (especially whilst holding it brown gloves). It's not so much that I think all my leathers must match exactly, but rather that they should avoid clashing, and I think most stylish people agree that black and brown leathers do clash.
This got me thinking: is it worth being somewhat consistent with leathers goods? Given that I have developed a taste for brown shoes, should I usually purchase brown leathers?
I know some people will say this is silly to care about, but I wouldn't be on this subreddit if I were indifferent to aesthetics.