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Yeah, I can totally see how the Cat and Cloud apparel line could be mistaken for that of Caterpillar

Not the issue. The issue is that they've registered a trademark for apparel with the word "Cat" on it, and Caterpillar already has one. If Caterpillar doesn't challenge it, their trademark could be construed to be diluted. If Cat and Cloud had just printed their logo on t shirts and hats and sold them, there'd be no problem. But by registering the trademark in an area in which Caterpillar already has one, they've run into trouble. Frankly, their trademark lawyer, if they had one, should have warned them. I run things through legal for a trademark search all the time and frequently get the response that pursuing something would be "high risk," as they put it, in very similar circumstances.

Except "CAT" and "Cat & Cloud" is NOT the same thing. From my understanding, you don't trademark a word, you trademark a logo or a design. If you want to register just a word or words, that falls under copyright / service mark. So unless Cat&Cloud is using Caterpillar's actual CAT logo (or something VERY similar) in their Cat&Cloud stuff, this doesn't apply.

Also, why should Cat&Cloud not trademark their own stuff? So the next guy can just use their logo no problem? Why should Caterpillar be able to block any usage of the word "cat", but Cat&Cloud can't protect their own "Cat&Cloud"?