At just 'bout any time, I will have Leatherman Wave, sharpening stick, keys with P-38 and Hot Spark, either Mini-Mag 3w led or Surefire G-2 with spare batteries, cell phone, credit cards, pocket change and cash, plus a couple hundred in hide-out-money, dogtag chain with micro light (brand unknown, it was a gift. Has three different levels of light, three speeds of flashing, and SOS flashing modes) and red dogtag with med info on it. Bandanna and a pocked pack or two of Kleenex. That is my bare minimum everyday stuff. I normally wear either low top "hiking" shoes or combat boots. If my other stuff gets squashed as you describe, depending on where I am, things are gonna get rough.

In your case, you really need to look for better footwear. I can't walk a few blocks in "dress" shoes...