Can a prone or unconscious character with 'Winged Boots' equipped still be safe from crashing?

Question

According to DMG p.47+: A flying creature can crash under certain conditions, e.g. being knocked prone while flying. Crashing itself is descried as falling and taking damage.

The item 'Winged Boots' has a property that you take no damage from a fall.

Winged Boots Level 13 Rare
These enchanted boots protect you from falling damage and can be activated to allow you to fly.
Feet Slot 17,000 gp
Property You take no damage from a fall and always land on your feet.
Power Daily (Minor Action) You gain a fly speed equal to your speed until the end of the encounter.

I was wondering if the property of the boots is still applicable if the character is knocked prone or unconscious?

e.g. I would expect a character to still take damage if he falls for more than the 'Safe Distance' because he is not really standing anymore. I don't really know if this is correct interpretation of the rules. If someone is diving down, head first, would he still land on his feet?

Answer 1

The rules are clear on this: the boots' property works perfectly and automagically so long as they're on the character's feet.

Many magical items have a special property which is constantly active, or active in certain circumstances. A property doesn't normally require any action to use, although some properties allow the user to turn them off (or on again). Unless otherwise noted, a magic item's property remains active for a creature only while it wears the item (in the case of a wearable item like a suit of armor) or wields the item. [Rules Compendium 280]

So unless and until the boots come off, or some other power or item explicitly interferes with them (mechanically, not just narratively), even an unconscious creature wearing them will land on his feet after a fall. He will probably then promptly gain the prone condition again, but that's not the boots' fault.

Answer 2

I don't think you're going to find a written rule on this, so it's going to be up to your descretion as DM.

My reading is that the winged boots would offer more protection from falling than being a winged creature.

A winged creature may suffer damage while flying that would impede its ability to fly because the wings are a part of its body and it needs to control them.

The winged boots, on the other hand, are in some sense independent of the creature. I don't read that description as requiring the wearer to be conscious to get the benefit of taking no damage from falling and always landing on their feet, because that effect does not require an action.

So I would say that yes, even if a character is unconscious and diving head first toward the ground, the boots will magically slow his fall and get his feet under him so that he lands safely, feet first. Of course, if he is unconscious, he will then crumple to the ground, but I wouldn't expect him to take any damage doing that, unless he landed among jagged rocks or something.