How do I do this? With select case and if statements?
Sure. Are you assigning these items to "slot" properties on the NPC? IE., a Clothing_Torso property could be set to some shirt item:
property <NPC; Clothing_Torso = White_Shirt>
If you do this then you don't need the unique values on each clothing item, I don't think. You could just test all the clothing properties of the NPC to determine if they are wearing anything. If the slot property equals some standard null value when it is not referencing a clothing item (such as NULL), or the NPC just doesn't have that property, then you know the NPC is not wearing anything in that slot.
It also depends on how descriptive you want to be.
[list]>look Joe
Joe is wearing a white shirt, a pair of jeans, and a set of black boots.[/list:u]
As opposed to...
[list]>look Joe
Joe is wearing a flowing white shirt, untucked over a pair of faded jeans. Polished black boots glisten in the sunlight.[/list:u]
The first one is easy to implement, the second a little harder.
Of course, if the clothing items are not referenced in slot properties (they just have a 'worn' property flag) then you'll have to implement the description in a slightly different way.