Couple of comments:
(1) Pitti is much more about fashion than understated style. The brands, products shown - and the buyers / attendees as well - reflect that reality. Showcasing trends, new products / designs is a priority
(2) The photos you see are of people whose business often depends on being noticed, photographed, and essentially advertised. The clothing choices they make during these 4 days is aimed towards receiving that free publicity and PR
(3) It's a clique. A couple dozen dudes, a dozen bloggers, constantly feeding off each other. You scratch my back, I scratch yours.
(4) there's an element of humor that can or cannot be appreciated
(5) some guys push the envelope but actually look really really good. Not in a classic MC way but still look good. Agyesh (shorter guy with the tulip hat) is a great example of that. He's got his own style, and of course he's in the business of promoting his company's stuff and new designs, but he has excellent taste.
I agree that Pitti is more than what tumblr makes it out to be.. No. 3 is what doesn't sit well with me. At least the other folks there are for legit reasons.