D&D 5E Werebear wardrobe malfunction!

[MechaPilot]

Assuming the wearbear has full control over his ability to transform, unless the axe is magical or does substantially more damage than his bite and/or claws, I don't really see why the werebear would care about keeping the axe with him.

As for the clothes, unless you're running a PG game, or there are other intervening circumstances, I'd let him not care. I recall the look of bemused shock on player's faces when I first described a werewolf charging at them, his were-doodle flopping menacingly with each stride.

 

[Jediking]

Per the 5e srd for the PHB Druid:
"You choose whether your equipment falls to the ground in your space, merges into your new form, or is worn by it. Worn equipment functions as normal, but the GM decides whether it is practical for the new form to wear a piece of equipment, based on the creature’s shape and size. Your equipment doesn’t change size or shape to match the new form, and any equipment that the new form can’t wear must either fall to the ground or merge with it. Equipment that merges with the form has no effect until you leave the form."

So I'd just copy that for the Werebear, and that his equipment merges into his form.

 

[Oofta]

Per the 5e srd for the PHB Druid:
"You choose whether your equipment falls to the ground in your space, merges into your new form, or is worn by it. Worn equipment functions as normal, but the GM decides whether it is practical for the new form to wear a piece of equipment, based on the creature’s shape and size. Your equipment doesn’t change size or shape to match the new form, and any equipment that the new form can’t wear must either fall to the ground or merge with it. Equipment that merges with the form has no effect until you leave the form."

So I'd just copy that for the Werebear, and that his equipment merges into his form.

The monster manual specifically states: Any equipment it is wearing or carrying isn't transformed.

Whether it matters or not is up to the DM of course. Personally I'd just give the werebear purple stretch pants and call it a day.

 

[Tony Vargas]

- make it a magic item which melds into his claw when he transforms into pure bear.

Rite of Talisman Dedication. In Werewolf: the Apocalypse 'Garou,' faced a similar problem, since they were spirit-magic-using werewolves, though, they had a solution, a ritual that bound an item to them so that it merged into an alternate form when they used it. Specified which forms the 'talisman' was present in when performed. So you could have had an ax in human and crinos (hybrid) but not in wolf form. Magic items are few steps up from a mere ritual spell, but might be reasonable if it's an important NPC and there's a reason for him having the goods. Otherwise, maybe he 'has the Ritual Caster Feat' and knows an unusual spell? Or just change the way the Wearbear transformation works to be more like the Druid's.

 

[Shrapp Hamnier]

As for the clothes, unless you're running a PG game, or there are other intervening circumstances, I'd let him not care. I recall the look of bemused shock on player's faces when I first described a werewolf charging at them, his were-doodle flopping menacingly with each stride.

ROFL. As fun as that would be, I really should keep this PG. I might loose half the party due to parent intervention otherwise. Participants are between ages 19 and 11, and the mother of 3 of them is a stickler for no exposure to anything crude. (I'm the same religion as she is, but she is very much more on the extreme end)

I'm upping the level of the werebear to around CR 17ish, he is hand picked by a demon king to be in charge of one of his secret police forces. So I want him to have some really strong attacks, and some nice incentives for defeating him (a sweet magical axe is a pretty strong incentive).

Thanks for all the input. I didn't even think about the clothes, I'll probably say that anything bearskin he wears merges into him. Though I am REALLY tempted to actually give him the purple pants. I may use them initially until someone gets the reference, then tell them his correct attire.

 

[Knight_Marshal]

Make the items he carries meld into him as the magical nature of the transformation and they become small patches of fur shaped like the item. Give the players a check to notice the were bear has a part of his fur colored in the shape of an axe.