Quote - Thing is I've never seen any detailed dynamic clothing.

 
Well, now you have!

Quote - I'm making something with zippers and pockets with an elastic waste band. I automatically assumed it had to be conforming.

For something tight-fitting like a jumpsuit, yeah imo it makes all kinds of sense just to rig it the same as the character it's designed for.  However for anything baggy, it will ALWAYS look better if it's at least partially dynamic.  Snug bits like your hypothetical waistband can be either constrained, or rigged as conforming, and the baggy bits attached to it could be dynamic (this is known as "hybrid" dynamic/conforming clothing).

Quote - The other question I had, how is dynamic cloth applied to a specific figure. People generally want to load their figure, load their clothes and props and click "Conform to". Can you set up dynamic clothing to slap on to a specific figure?

If you have enough polys to work with, pretty much any dynamic clothing item can be fitted to pretty much any character with a little fussing.  Basically, load the figure at zero pose, and set up a cloth simulation to run for 30 or 60 frames; at frame 1, the character is at the default morph/scale/whatever.  At the final frame, dial all your morphs up.  When you calculate the simulation, the character wil gradually morph from the default shape, to the target shape, and the clothing item will stretch or sag to fit.  There are various tricks to make this work better like scaling your character down at frame 1, or making them flatter or whatever, to fit into the dynamic clothing at the start of the simulation. See Phil Cooke's many tutorials on this.
www.philc.net

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