I like o/o's look. It's right in line with his go-to-hell, bigshot dandy style that he's seemingly cultivated over many years. I think it's a signature look, a bit eccentric but more interesting and well considered than most. Probably not right for this particular thread, though.
Mike, not really digging these. The first is great, except the pocket square appears totally random. The second is okay, but you know how I feel about triple solids--particularly solid squares paired with solid shirts.
That dark green Drakes square is very hard to photograph - I know from experience... It really is not that strange birdpoo green you see here. Knowing what it really looks like, I think it would work well with the rest