Devoa/Begg/Frank Leder/John Elliott/IE/m_moriabcPhotos of me putting on boots because c4est found the laces amusing (Click to show)
I think looser could be cool, yeah. These are a bit funny though on me - the way the fabric drapes, and the way it interacts with the lining, it keeps the legs sort of "inflated". As in, they make my thighs look much bigger than they are when I'm standing still. It's sort of cool though, but the pleats and soft fabric make them some of the most comfortable and accommodating trousers I own.
Compared to the Paraboot, I would say these are much sturdier, so it's different both in feel and vibe. The sole is stiffer and more structured, the leather is also stiffer and thicker, and the shoe as whole has a little more presence. I think these qualities work really well in this specific color, but if I wanted a similar pair of shoes in black, I would probably go Paraboot. What makes these work is the specific combination of design and leather.