Cozy ambient inside, but also with tables on the street, Champagne Socialist is a good place to try natural wines from Europe. You can also go there just to buy a bootle (or more, of course) and drink it at home.
Gramm Cafè is a super lovely place, born just few months ago in the warmest part of Milan: Navigli. Great for sharing some moments with friends, tasting great quality cocktails in a stylish designed interior. One of the best drink is for sure "Prete Rosso"!
Nice atmosfere, cool staff, opened from the first time in the morning til late night... Iter is a good choice for breakfast with coffee and brioche (the way Italians call the croissant), working days lunch (the have a fixed menu) and also for drinks - the menu changes seasonally and has always interesting options. Thanks to its location in a small street between the naviglio grande and pavese, the tourists somehow don't find it.
To really reach/understand a city you must live there or, at least, acting like you do. Nothing makes you feel more like a Milanese D.O.C. than stopping by Frida's on a Sunday morning to buy some flowers. Located in Brera this tiny shop has an extraordinary colour palette of flowers and plants. After that we just take a walk in the neighbourhood holding our bunch of Brassica Oleracea and our day is made.