I can relate to this fellow as if it were not for the lack of a clipless shoes that I'd like to wear I may be using clipless pedals on my drop bar bikes, that includes the Bomba. I see nowhere of Mr. Peachey actually saying "screw you" to any notion of wearing wool and leather though, hah hah. If I had a Playtypus I'd set it up as a road bike too, with drop bars.
Regardless, I wear Sportful road clothing: bibs, jerseys, jackets and leg/arm warmers. I had never actually tried anything but the form fitting bibs, but then a few years ago I got some jackets and jerseys. All I can say is I'm so much more comfortable riding in any conditions, notably between 32 and 65 degrees. The various jackets far surpass any non-cycling method I had tried to stay comfortable in the cold/wind or now even the heat. I was adamantly "wear non-cycling clothes" for about 15 years and it basically sucked. I went back to wearing bib shorts again and form fitting baselayers and now road jerseys and jackets and am over the moon with it all. Plus, I like the Sportful Italian design style, it's not only functional but is very dapper looking.
I can relate to the downslope of his saddle in the photo. Not quite that much, about 2d down nevertheless. I had never even considered that before but on a whim of experimentation I tried it, and laughed all the way in finding it the most comfortable and efficient setup I've ever had in my life. Ritchey Skyline Comp saddles, and I sit relatively far back on them so the bony sitting part of the pelvis is right on top @the wide spot and provides a stable platform to push on the pedals from. Whatever works !