Fair warning that this may be controversial.
Vans AVE Pro (and every other Vans shoe in the last 20 years)
Although the suede is indestructible, I blew a hole through the mesh in less than an hour. It has no support or cushioning whatsoever, and is just an uncomfortable, flabby mess of a shoe. All Vans are utterly unskateable.
Adidas Puig (and every other popular model I've tried)
Same as the AVE, but even more uncomfortable. There's always a hard seam right behind the toes that digs into your foot. All Adidas manage to be hard/stiff feeling, but somehow still don't offer any support or cushioning. The Puig looks like the perfect shoe for me, but my word did they fuck it up.
Nike Koston 3 Hyperfeel (the sock shoe)
Garbage. They squeezed my feet in all the wrong places. The sock liner was supposed offer extra stability, but I felt like I was gonna roll my ankle just pulling up to the spot.
Just to clarify, I'm not looking for chunky, thick and super supportive shoes. The 1010 for instance is too thicc for me. The beforementioned shoes simply suck my taint, and you're simply just wrong if you disagree. You'd be better off tying a vulc sole to your feet with some shoe string.