Expectations vs. Reality
Before coming to Milan, I read and was told that it's "more modern than other Italian cities," "doesn't have too much history" (in terms of historic sites, buildings, etc.), and of course, that it's "the fashion capital of Europe." I had expectations of towering buildings and modern architecture looming over its ultra-fashionable population. These expectations were questioned a bit as my plane began to land; as we flew over the city, I noticed there were no skyscrapers in sight.
I was right about the lack of history, however. Though Milan was the seat of power on the Italian peninsula for quite awhile back in the day, very little remains of its former glory. A few remnants of the Roman walls still dot the city, various cathedrals and basilicas are tucked away among apartments and shops, and of course, there is il Duomo. However, Milan lacks the awe-inspiring glory of monumental historic sites found in other Italian cities; the Colosseum in Rome, or Brunelleschi's Duomo* in Florence, for example.
As a foreigner living in Milan with a strong interest in history, I consider this a blessing and a curse. Sure, I'd love to have a massive list of places to visit and study right at my doorstep. But because Milan lacks these structures, it doesn't attract as many tourists as the other more historical cities do. What it does have can often be enjoyed in relative peace and quiet, especially in the off-season.
*Duomo just means 'cathedral,' by the way