Too cool for you
At first sight Milan is really a piece of shit. You arrive at the dangerous, junky-ridden central train station and really hope that you don’t have to catch a night train or bus around there.
Things don’t really improve as you go into much of the city and find grey concrete blocks, hostile and snooty people and the general indifference to humanity common to most big European cities.
Perhaps Milan could be worthwhile visiting or living in if you were heavily into art and design – some of the world’s greats live and work here and there are any number of shows and exhibitions to check out. Unless you dressed the part though they might not let you in.