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The SRD's entry for the Cloak of Charisma says:

This lightweight and fashionable cloak has a highly decorative silver trim. When in a character’s possession, it adds a +2, +4, or +6 enhancement bonus to her Charisma score.

Emphasis mine. Rules-as-written this means you don't have to wear the cloak in order to get the bonus. I understand it's ridiculous to interpret the rules as they are on the SRD, as that would mean you could "wear" two magical cloaks while having one of them in your bag. I wonder if this wording was intended, or a typo of sorts, out of plain curiosity.

Did the designers intend that meaning, or is this just a really big typo of sorts?

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  • \$\begingroup\$ Interesting to note is that this is the only item in both the DMG and the MIC that uses this phrasing to describe any item. In the MIC it says "+2 enhancement bonus to Cha" as its description. \$\endgroup\$ – Thomas Jacobs Nov 4 '15 at 17:56
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    \$\begingroup\$ Maybe they wanted to allow you to be 90s charismatic and wear it around your waist or 2000s charismatic and wear it like a scarf. \$\endgroup\$ – user25296 Nov 4 '15 at 21:34
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For safety's sake, I urge against trying to convince all but the most serene DM that keeping a cloak of charisma in a backpack still enables the possessor to gain its benefit. Dice can hurt when thrown hard enough. That said...

It's possible (but unlikely) that the designers intended a cloak of charisma to be kept in a creature's possession instead of actually worn...

I've not heard anything from Monte Cook et al. about this (and such industry figures are unlikely to respond to my queries anyway), but the Dungeon Master's Guide on Using Items says

Continually functioning items, such as a cloak of resistance or a headband of intellect, are practically always items that one wears. A few, such as a pearl of power, must simply be in the character’s possession (on his person, not at home in a locked trunk). (213)

Emphasis mine. An argument can be made, then, that picking as an example the cloak of resistance when the cloak of charisma is the obvious alphabetical choice speaks to designer intent: after reading (or even writing!) the passage quoted above, the designer of the cloak of charisma—such an argument would go—seems to have wanted to exclude a creature from needing to wear a cloak of charisma to realize its benefit and carefully phrased the description so that such a cloak could be shoved into a haversack and its possessor could wear instead, for example, a cloak of resistance.1,2

...But it's strongly implied that any magic cloak be worn to gain its benefits

The Dungeon Master's Guide on Magic Items on the Body says

Many magic items need to be donned by a character who wants to employ them or benefit from their abilities. [...E]each of those items must be worn on (or over) a particular part of the body. A humanoid-shaped body can be decked out in magic gear consisting of one item from each of the following groups, keyed to which place on the body the item is worn.[...]

  • One cloak, cape, or mantle around the shoulders (over a robe or suit of armor) (214)

So while an argument can be made for still gaining an enhancement bonus from a cloak of charisma +2 folded up in a backpack, that's not how a magic cloak is employed by one who wants to benefit from its abilities. A cloak of charisma is not a chaos diamond or a stone of controlling earth elementals or even a luck blade—all of which require possession but having types that aren't listed on that chart. The cloak of charisma is a specifically noted type of magical item that occupies a body slot, a cloak.


1 Maybe that designer was playing a sorcerer?
2 However, truly first alphabetically among the Dungeon Master's Guide's wondrous items is the amulet of health, and that item needs to be worn, so make of that argument what you will.

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To expand on the previous answer, the pricing rules for magical items also heavily implies that the Cloak of Charisma needs to be worn in order to function. If you have a look at Table 7-33: Estimating Magic Item Gold Piece Values, on p. 284 of the DMG you'll see that under Special Considerations an item not taking up a slot (no space limitation) is considered. What it says is that when an item doesn't take up one of the slots defined in Body Slot Affinities on p. 214 of the DMG the entire cost of the item should be doubled. Since a Cloak of Charisma+2 doesn't cost twice as much as a Headband of Intellect+2, it seems a reasonable reading of the Cloak's description (more specifically its cost) that it needs to be worn as well.

A possible argument against this is the Behind the curtain: Magic item gold piece values blurb on p. 282 of the DMG which states:

You’ll notice, however, that not all the items presented here adhere to these formulas directly. The reasons for this are several. First and foremost, these few formulas aren’t enough to truly gauge the exact differences between, say, a ring of fire resistance and boots of speed—two very dissimilar items. Each of the magic items presented here was examined and modified based on its actual worth. The formulas only provide a starting point. The pricing of scrolls assumes that, whenever possible, a wizard or cleric created it. Potions and wands follow the formulas exactly. Staffs follow the formulas closely, and other items require at least some DM judgment calls. Use good sense when assigning prices, using the items in this book as examples.

Personally I'd argue that a Cloak of Charisma+X is mechanically simple enough that it probably follows the item-creation rules as written.

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