I've taken too many trips where I unpacked unused clothes afterwards, so I try to be really strict with myself!
For warm clothing on most trips, I stick with a really good quality waterproof & breathable jacket for both wind/rain. I buy nice looking ones that are a bit dressier if I can, although these tend to be more pricey. For my warm layer (for women) I now bring a thin wool cardigan. Again, I buy a rather expensive one and in a neutral color that I can wear casually or dress it up with a scarf. These work so great and are very warm. A fleece in addition to this for more casual wear is a lightweight addition that should be enough layers for most destinations. I highly recommend the LLBean Fitness Fleece, which I've purchased many of over the years. Stretchy, warm, zip pockets, perfect!
This was a great article. I've become overwhelmed with packing advice at this point, but I liked the simple advice in this article which has helped me think through how to pack stuff really tightly and efficiently.