I live 10 minutes away from my work, minus the heavy construction lately, more like an 8 minute drive/ride. I have always worn my jacket, gloves, and helmet. Recently I let my good friend take my 250r for a ride, his first, and I made him wear the gear. Unfortunately he dropped the bike doing about 5-10mph on a side street doing a u-turn. Messed his ankle up pretty bad and had it not been for my jacket, which is now pretty banged up, he would have had some serious road rash up his left arm. Now granted this was a rookie mistake and his first ride, but nobody can avoid riding through a mysterious puddle of oil/anti-freeze, or hitting some unexpected gravel as they head off to work. My opinion (re-enforced by this experience): Always wear your full gear, no matter what, no matter how short the distance, or how cool you might feel just taking her for a ride around the block. Chances are, you will be fine, but on the off chance that the unexpected happens, you will be so grateful you did. End of story.
Side note: he will be ordering me all new parts for the damage he did to my bike, like a good friend does.