Back on July 11th, I posted this:
Unlike my other postings this morning, shirtless men will not come into it. That is, this posting is shirtlessnessless.
Yes, shirtlessnessless. The formal pattern here is indefinitely extendable, but rapidly yields words of vanishing utility in real life.
(1) -less combines with a N to yield an Adj meaning, roughly, ‘lacking N, without N’: hope → hopeless, fear → fearless
(2) -ness combines with an Adj to yield a N meaning, roughly, ‘the property or state of being Adj’: happy → happiness, thick → thickness
(1) and (2) are obviously meant for one another. Start with the N shirt. (1) gives us the N shirtless ‘lacking a shirt, without a shirt’. Then (2) gives us the N shirtlessness ‘the property or state of being shirtless’. From there, we pingpong back to (1) and get the Adj shirtlessnessless ‘lacking shirtlessness, without shirtlessness’ — in the case of images, that would be ‘having only shirted images’ or ‘fully shirtful’ (however, though the Adjs in -ful corresponding to those in -less are interpretable, they often don’t feel idiomatic, as in this case).
One more step gives us the the N shirtlessnesslessness ‘the property or state of being shirtlessnessless’ — that is, ‘the property or state of having only shirted images’, or more succinctly, ‘shirtfulness’. This is where things run down on the practical side of things, since we’re only getting more and more indirect ways of conveying a few meanings, and these forms of expression are useful only if there is some point to the indirection, some subtlety that would justify the choice of the more indirect over the more direct expression; using the more indirect expression implicates that the more direct expression is in some way inappropriate in context or imprecise.
(The process also works starting with -ness rather than -less: happy → happiness → happinessless. But now we begin to run down, since happinessless could normally be expressed by unhappy. And it’s really hard to see a use for happinesslessness.)