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1.
(Adj) A physical appearance suggesting an individual has lived a tough existance; usually as a result of substance abuse. The term originates from the distinction between a car that has "city miles" versus "highway miles."
I really don't believe that Kate is 32. If she really is that age, she's got some serious City Miles.
by SquareMike Jewpants November 18, 2004
 
2.
To describe the amount of sex partners one has had.
That girl has slept with so many people she has city miles
by Bill Knapp April 28, 2005