Should I Wear a Black or Brown Bag More Often in The Winter?

Fashion dictates that black is more formal that brown. I am not talking about "dress" bags though. I am talking about everyday I reach and go. Should I wear black to the office and brown otherwise. Should I always match my bags and shoes? Should it always depend on what I am wearing? I am just looking for a good "utility bag" because changing my bags out is not very much fun, but necessary sometimes. Should I wear this brown or black bag most of the time in the winter?

#1 My Black Bag
#2 My Brown Bag
It Depends on What You Are Wearing
It Doesn't Matter Anymore. Wear Whatever You Want
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Should I Wear a Black or Brown Bag More Often in The Winter?
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