It's a crap look, no doubt. There are ways to do the jacket with jeans thing, but emulating German businessmen is no way to do it. For one thing, the jacket should be quite fitted with high gorge and be make in a more casual (i.e. more textured) material - moleskin, brushed twill, corduroy, even velvet. I.e. your Cloak NYC jacket will work, your Barbera will probably not, even though the second is better made. The second thing is, don't tuck in your shirt - never tuck in your freakin' shirt. If it is too long and/or billowy, it probably should be worn with jeans anyway. Try Costume National, Prada, or Helmut Lang shirts for a sleeker look; Age, Coast, or Steven Alan shirts for a more casual look. If you think this looks a little messy, put a fitted, v-neck over the whole thing. The tie should be loose on the collar or done away with altogether, especially if you are not wearing the sweater. The jeans should be fitted and low rise, but not too fitted and not too low rise. The first, and you are a German businessman (congrats), the second, you are too Dsquared for Dsquared. The last thing is the shoes - they should be shoes that go well with jeans - desert boots, sneakers, chunkier chelsea boots, Docs. I don't care if your John Lobbs were bespoke or not. You look like an idiot irregardless of the costliness/beautiful worksmanship of your shoes. Some Italians do it, yes. But some Italians are idiots, and the ones that oul it off are probably a lot better looking and naturally cooler than you, oh shopper at Barneys and Bergdorf. Let this be a lesson for all of us. Just because you are wearing top quality doesn't mean that you are going to look top quality - you gotta put the stuff together right.