Steve Jobs should be definitely be commended for selecting clothing items that using the Goldilocks "just right" standard appropriately fit (i.e., he is not in the grubby looking grossly oversized and prison inspired garments or trying to squeeze into skintight jeans) and worn in a neat manner (shirt tucked in, shoes tied, etc.) suitable for any causal encounter.
While you personally might not have worn all three items together, I find it hard to believe that guys here have not at sometime worn: a mock turtleneck, Levi's blue jeans, and New Balance sneakers. Sure, the fancy turtleneck give the outfit a little class, but it is basically what a lot of men wear when they take the dog out for a walk. So, in answer to question, yes I'd wear what Steve has on and have on many occasions had on an analogous outfit with different color turtleneck, slip-on loafers instead of sneakers, etc., but for me it is not a daily "uniform" with the same colors as he has made it.