Yeah Supreme seems arrogant because they seem to be riding off reputation and their longevity in skateboard culture rather than coming up with some actual dope and creative concepts.
For example, I'd like to know what effort they actually put into coming up with these construction Timberlands...
supreme-timberland-6-premium-waterproof-boot-02-96
So it appears the only thing they did was make the upper area around the ankle a reptile texture, and then slapped a red Supreme tag on it. That's it. And they instructed people to pay extra money and camp out just because of that little red tag.
Those Foamposites they did were ugly and gaudy as fuck. The stuff they come up with either is very simple, boring, and unimaginative -- or it's over-the-top and ugly.