I suspect that bike-shedding is the major issue.
If you are going to wear a suit, wear one properly.
He would be ahead (at least in my mind, not that my opinion matters) if he just wore properly fitting slacks and a polo vs an ill fitting suit. He'd be better off wearing a hoodie and jeans too because at least then we know he doesn't have any respect for the idea of "dress is important"
EDIT: Fixed spelling
Do you think his business would run better if he wore better fitting suits?
But Dell is wearing a suit which means that he in some way feels it's necessary to do so. But he does such a bad job of it that even a glance makes it obvious he doesn't know what he's doing. Or the person he paid to get him a suit did a horrible job. Given that he's "running" a $24 billion dollar company I would like to see better attention to detail on a thing that he must think is important, as evidenced by his wearing a suit.
It's worth noting that Dell is a Texas company, and the t-shirt and jeans look is still a pretty specifically SV trend.