Hopefully we can all learn from our unfortunate 2-wheel comrades the importance of proper gear, including boots. This notion that it's too much trouble to put on a different pair of shoes, or that it takes away from the joys of riding to wear a full-face helmet and jacket is just ridiculous. I for one get a much greater sense of contentment when I ride knowing that should the worst happen, I've done everything I can within reason to mitigate and manage risk and injury.
Well said, as was DennisD's comment about "rolling the dice". And it's precisely my point! If you've been riding for a while and hanging out on different moto forums, you read about folks getting really messed up without gear and other folks surviving surprisingly bad encounters while wearing gear. I just read a new one today on the Ducati MS board about a guy and a deer. Suffice to say, his gear saved his ass. It's unlikely you'll encounter a deer on the typical scooter ride, but that unleashed Golden Retriever can do just as much damage.
Riding a bike is unpredictable. The more miles you pile up, the higher your risk. Sure, you're more experienced, and that helps, but you're also exposing yourself more often to random dangers. Inattentive drivers, deer, daydreaming bicyclists, big dogs, sand, gravel, choppy pavement, oil or grease and a host of other risks. I was riding home last week and something hit my helmet really hard. Acorn? Bird? Big bug? I have no idea, but without my helmet it would've hit me square in the forehead and might have been enough to take me down out of sheer surprise.
Do I fully gear up every time I ride? No, there are times when I'm going a few blocks to pick up milk where I take shortcuts. Usually, once I'm a block or two from home, I'm thinking I should have taken the extra two minutes to gear up. I hardly ever shortcut helmet, gloves and boots though because that's where the most significant damage tends to happen. And when I say "hardly ever", I'm talking about maybe once a year for some lame-assed reason.
As for boots, I tend to go with moto boots for a couple of reasons. One, already mentioned, is waterproofing. I have an old pair of Tourmaster boots that are my everyday scoot boots plus a newer pair of Sidi Sport Tepors. Both are comfy, fine for walking and completely waterproof. Nothing worse than ruining a pair of boots or shoes when stuck in a downpour.