I think Timo has made better choices across the board (with the exception of the DB-ness of the blazer)
So, first things first, should be a SB. I don't like DB odd jackets and like them less with knakis.
Shoes - suede bluchers are pretty much bang on in terms of formality for a khakis with jacket look. Shiny shoes always look off with cotton unless they're loafers.
Consistency - everything (again, ignoring the DB-ness of the blazer) is about the same level of dressy casual. The blazer is lighter so not so severe. The pants are pressed. I'm assuming the shirt is solid and it's not a BD.
Timo isn't just consistent in terms of formality, but also in terms of seasons. Everything looks springy - the colors and materials all look like they're made for warmer weather.
Stitchy, on the other hand, has very shiny shoes with very rumpled pants. And a autumny-looking SC (due to the fuzziness) with cotton trousers. It's a mix of sesaons.
But IS also has a suburban biz-caz (comfortably cut khakis + a very Brooks Brothers looking shirt) with a luxe-looking SC.
I have not made this comparison to pick on Stitchy or to hurt anyone's feelings. I think these two photos illustrate some worthwhile points. If you disagree, feel free to send hatemail.
the SC is decidedly not autumn-y imo, maybe you have to see it in person. it is a very light (both in color and weight) 100% cotton fabric, with 3 patch pockets and pick stitching all around. i think the formality and seasonalness (nice word, amirite) of both is quite equal. they both, imo, lend to a bit of a washed out/worn look, which i like in this context.
the shirt is a tad more dressy, and not what i would have picked optimally, a mid size slubby cotton gingham might be cool, or a solid BB OCBD, ill give both of those a try at some point.
the shoes, yes, they are decidedly more dressy than the rest of the fit. even though i view a monk strap to veer on the casual side of dressy, its still more dressy than everything else. that was an intentional choice, its kind of #menswear inspired, but i wanted to do it, and i think its ok. be prepared to see these pants in the future with these shoes, shiny carmina calf light tan/chestnut DMs and suede GG st james IIs. its not a look everyone will like, certainly not one who is strictly a "good taste" follower, but i dont think its egregious, and i do like it.
i think timo looks great, no doubt, but i think he and i were not really aiming at the same target with out fits.