Having read this whole thread, y'know what's even better than wearing the same thing every day? Not wearing the same thing every day. I have a bunch of different clothes, and deciding which of 'em to put on really doesn't take that much time out of my day.
People who say suits are uncomfortable have usually only worn cheap suits.
One thing there's still a dearth of in the marketplace is men's trousers with stretch. I had a pair of gray stretch cotton/spandex (~5%) slacks from Banana Republic 8-10yrs ago that were absolutely perfect for anything, but haven't found much else similar since.
Imho, a simple wardrobe is great but being able to execute on the plan depends wholly on one's lifestyle.
I love my city but two things I can never defend: the heat and the traffic. Aside from that it is heaven on earth.