FWIW, as Derek has pointed out before, he doesn't dress like a blogger. Bloggers dress like him. I still am not really a particular admirer of his style in general, nor this coat in particular, but give the man his due.
I don't think there's all that much difference between the two.
They both have quirky and - I imagine in Wooster's case as well - very firmly held views on what looks good. They both value complexity in outfits and have a thing for garish oversized details. Each is likewise inspired by traditional American steez.
The results are different because one sells clothing and the other sells companies but I think the processes and sensibilities are eerily similar.