Good topic, always a headache balancing items you would like to carry 24/7 with the rules and laws in your particular environment.
Personally I will always have on me:
Leatherman Wave
Zippo Lighter (normally accompanying a pack of Marlboro)
550 paracord cobra-stitch bracelet (in Coyote fyi)
G shock watch (analogue so can be used to find north/south)
Wallet, Phobile Moan, Keys on a two foot length of cobra-stitched 550 paracord (black)
However I am also a biker (or motorcyclist if you prefer) and whether in the UK or overseas I spend most of my time in an office I have a daysack i've been using for a few years
Picked it up at a local surplus store when I bought some kit and remembered I had to get them home somehow. Once I'd cut the hip belt off (as they're a waste of time on these little bags, and will do more harm than good) and added a few other mods, it has served me non stop in all weather, and travelling overseas.
In this bag I'll also keep:
Electrical Tape (better than plasters and more useful)
£20 in baggie
Maxpedition Ferox folder (black) - this recently replaced a SOG Fielder XL, which I felt was a bit flashy due to the polished steel
50ft 550 Paracord (olive)
Plain business card with a few essential phone numbers on it (no names. I find remembering a hand full of 11 digit mobile numbers a challenge. So I wrote them down, remembered the order and then taped it up with clear nasty to waterproof it, ish).
Tactical Pen
Sharpie
Fingerless Wool Gloves
Shemagh
The real pain is when I go overseas, its normally just for the day (or two) so dont take anything larger than my daysack and it goes with me in the cabin, so no sharps. I was considering getting a cheap multitool in each of the places I visit and finding or making a stash point.
With all that and my laptop, cables, phone charger, skivvies the bag does get a bit hefty, but like I said I am a biker and find those awesome kevlar armour shoulders on a bike jacket does well to ease the strain of the thin shoulder straps on the daysack.
When it comes to foot wear, I'll either be in a pair of leather Matahorn Gore-tex jump-boots if its cold or wet, or Grafter Dessies. After many many many years in boots I dont find trainers or civvi shoes comfy anymore and wouldn't be comfortable walking for more than 5 minutes in something that I know I can't walk all day in.
That'll do donkey.
If I can be arsed I'll take some snaps later and edit this post with em (if I can figure out how).
Peace, out.