Random food truck - Sustenance is key while trekking around in the biting cold. Give (decent-looking) food trucks a try with their unfamiliar albeit intriguing filling combinations and you might be in for a treat :)
Shockolat - Hands down, best gelato. Ever. My selections of nutella and dark chocolate surprised me in every way I didn't know it was even possible for gelato to taste that amazing. We stumbled upon this cozy place while on the way back from somewhere else - a little out of the main city center but so worth a visit!
Duomo - at all angles and times of day.
Pizza Pazza - A quaint little eatery just a street away from the main city center, with probably the BEST meals we had during the whole of our stay. Nothing fancy or pretentious, just great Italian fare that satisfied our bellies so much we made a return visit :) p.s. moral of the story - always make conversation with your cab driver and ask about their local hangouts!
It was a few nights in when I took a little wander on my own, and it finally sunk it that wow, I was indeed in Milan. There I was, standing in front of the magnificent Duomo (the fact that it took something like 450 years to be built fascinated me), right by the famed Galleries full of designer stores, in the midst of hundreds upon thousands of people. It was funny because for the first time then, the cold wasn't so unbearable - it was refreshing, even; it was a weird feeling of content, of being able to watch from the sidelines, of realising that everywhere in the world, you get people going about their busy lives, you have the street vendors and buskers and pigeon-catchers, you also see those who for some reason or other are less fortunate - it all is quite humbling when you realise that you're only one of the many billions in the world.
Apart from the sights and shopping streets, I was also looking forward to good food - which was a little bit of a hit and miss, really. I know many who have raved about the high standards of Italian food but I would still say, try to do some research and pick your restaurants carefully! There are indeed lots of overpriced 'tourist traps' around, and honestly even your hotel concierge might not be the wisest of advisors. In our case our cabbie was :) Luini panzerotti seemed to be the snack of choice for both locals and tourists alike and gelato-eating in freezing temperatures was completely routine!
Oh Milan, thank you for having me.