Umm, back from Aussie land---

Shoes and boots: not only comfort for walking, but consider waterproof and insulated depending on your climate. Mr. Murphy will see to it that when you are walking, it will be raining or snowing and there is nothing worse than walking in cold/wet shoes or sneakers. Frostbite is not to be fooled with.

And +1 on flashlight/headlamp. Not only while walking out, but the real problem is being in an interior room deep inside the office building and the power goes off. Hope the batteries in the emergency lights still work... if not, you will need that small EDC light in you pocket to find the rest of your gear.
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"Better is the enemy of good enough."