LOL -- Lisa and Sal!! I truly think both approaches have their benefits, and I, at the moment, am wrestling between two mindsets!
The up-side to "dressing like a billionaire" is how freaking fast and easy it is to get ready. One fabulous but simple coat works for most situations. If you're feeling fancy change up the accessories and you're done. And when it's really cold out, I tend to become less concerned with what I look like and more concerned with not freezing to death.
In this approach the coat becomes just a part of me -- like my hairstyle -- that also doesn't vary a lot from day to day. Or my car. It's part of the infrastructure.
However, I used to have a real weakness for buying outerwear on a whim. It was easy to try on and I had a major reason to own it -- dressing for the office. Now that more coats and jackets are likely to fit me better, we'll see if I revert to my old ways. Although the lack of need to dress for the office raises new questions about what I actually NEED.
Hence, I suppose, being ok with watching and waiting to see what crops up.
Saw a beautiful green Save the Duck puffer on Simon's website last night -- and fell off my chair laughing when it said it could withstand temperatures of -5 to 10 degrees C! Sadly, not even close to what's ahead. Sigh.
Thank you both for commenting!!!