Nothing here yet.
The thing that catches most men out with a jeans based outfit is the fit stacking up wrong across the whole look. You get the jeans right, slim through the leg, decent break at the ankle, and then put a boxy jacket or an oversized hoodie on top and the proportions go to pot. I spent a long time thinking jeans were the easy bit of getting dressed, the part you didn't need to think about, and they are, right up until everything else you pair them with fights for the same space. Get the balance sorted though and a good jeans outfit does more heavy lifting than almost anything else in a working man's wardrobe, because it looks like you tried without looking like you tried.
Where it comes unstuck is obvious once you see it: jeans with anything too formal above the waist, a sharp blazer or a proper collar and tie, start to look like a costume rather than an outfit, like you got half dressed for a wedding and gave up. Heavy work boots with slim tapered jeans can look top heavy too, the leg disappearing into a boot that's doing its own thing. And layering wise, a thick jumper over a jacket with jeans underneath tends to bulk you out more than it should, especially if the jeans themselves have any weight to them. The honest limit here is that this is a smart casual look at best. It is not going to carry you into a black tie situation, and if your workplace wants proper trousers, no amount of clever styling with jeans gets you there. Know what it is for and it stops being a problem.
What I will say for a good pair is that they age well if you treat them properly. Raw or dark denim softens and moulds to how you move within a couple of months, and that's part of the appeal, nobody else's jeans fit exactly like yours after a bit of wear. The trick is not overwashing them, turn them inside out, cold wash, and skip the tumble dryer unless you want the legs a size shorter by October. Check the stitching at the pocket corners and the belt loops before you buy, that's usually the first place things give way, and a bit of weight in the denim itself tends to outlast anything too light and papery.
This whole area suits the man who wants to look like he made an effort without admitting to anyone that he did.
Nothing here yet.