OTC FTW. Skinny trousers may not be friendly to them, but.../shrug
And don't sell wool socks short; I've found that a good merino wool is a great boon in winter and very comfy even on warmer days of fall and spring. The biggest advantage: they keep my feet bone dry. I wear Gammarelli and love them to death, and I'm likely to pick up a few Bresciani from Will at ASW soonish.
Really? The OP has a thought about what people should have to "avoid being poorly dressed" and, in that light, the navy blazer becomes even more essential in our modern "Casual-FridayEveryday" world. Any reason for dropping the navy blazer or just a generic anti-Brooks stance?