Okay so everyone told me Milan is a 1 night stop, just see the Duomo and move on. But I booked 2 nights there before Lake Como and now I’m second guessing. Beyond the Duomo and Galleria, is there enough to fill a second day? I’ve heard Navigli is cool for aperitivo, and there’s the Brera district? Last Supper is sold out for my dates already (of course). Would love to hear from people who actually liked Milan.
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Great question! Milan gets dismissed way too easily by people who treat it like a transit hub between “prettier” Italian cities. If you only do the Duomo/Galleria loop and leave, then yeah, it feels skippable. But if you lean into what Milan actually is (design, neighbourhoods, food culture, bars, fashion, modern Italy), two nights is a very good amount of time.
Milan has so much to see! I used to work in Milan and there are museums you can visit, I recommend the Leonardo Da Vinci museum and the Science museum. Sforzesco Castle and it’s park are a great place to relax. I am not sure when you are thinking to be there but around Christmas time, the city is also decorated beautifully with different lights and Italian designer Christmas trees! Don’t forget the Italian coffee is also amazing!
There are a lot cute smaller day trip cities you can do from Milan. That is what I would do and did do
I think you could easily fill a few days in Milan - I did! 
While I had a spare day in Milan I jumped on a train down the Cinque Terre coast line, it is a big day trip but if you just focus on 1 or 2 of the towns in the Cineque Terre rather than all 5 then it is a nice way to see the coast of Italy and stunning post card worthy places 
I actually really like Milan 
I worked in the textile industry for many years and used to visit Milan twice a year, so I got to experience the city beyond just the Duomo.
Two days is definitely not too much in my opinion. Brera is lovely to just wander around, Navigli is great for aperitivo in the evening, and honestly Milan has a very different energy compared to other Italian cities — more stylish, modern, and local-feeling.
If you enjoy fashion, design, cafés, window shopping, or simply walking around beautiful streets, you’ll probably appreciate having the extra day. And Lake Como right after Milan is actually a really nice contrast.