Yep. One (high level) druid trick is to move tons of loot by wildshaping into an elephant, loading up with giant saddlebags, then wildshaping into an eagle to fly to the destination. The loot is recovered by the druid wildshaping back into an elephant
Or more practically a druid’s bear form might wear armour that is too heavy for their normal form to carry
RAW that wouldn’t do anything though.
What do you suppose is gonna happen to the nails when the druid switches back?
Your worn items just kind of morph into your body when you wildshape. You don’t have to strip naked to go from humanoid to animal, for instance.
But does it work the other way around?
Yep. One (high level) druid trick is to move tons of loot by wildshaping into an elephant, loading up with giant saddlebags, then wildshaping into an eagle to fly to the destination. The loot is recovered by the druid wildshaping back into an elephant
Or more practically a druid’s bear form might wear armour that is too heavy for their normal form to carry