Great insights! I love the ON jeans. I am askeert to use the term “ classic” lest it be too boring, but the FIT , including length, has elegance, to my eye. That doesn’t mean that an outfit as a whole can’t be fashion-forward, nor that some other styles of pants that you also like might be more notably fashion-forward , but just a good thing to note, that these jeans provide you with a necessary element.
So, haha, my fave jeans this past year or so are also ON! In addition, they are more trendy for ME ( and my environmental norm) because they are somewhat wide—the ON OG loose. I could really use a slightly slimmer straight style as well because my target IS to look a bit more “ timeless” and I don’t want a large jeans capsule, so want to look for that ( but SO many jeans to try on). Mine are in about the same wash as yours though I was planning to buy a dark wash— for some unknown reason, the fits were different in different washes( I know fabric content could be different, but it was still weird). I found the lighter blue to be unexpectedly useful in winter as I wear browns but more taupey shades- important because it’s too hot for jeans here in summer.
I’ve tried numerous barrels and have given that style the ix-nay, also all wide crops. I do wear ankle- length if straight or a very slight taper, or BF if not low-rise. I think related to a combination of torso & leg length plus I can’t routinely wear low- profile/ pointy/ dainty footwear anymore for everyday occasions , and do not like the look of my lace-up sporty shoes with wide crops.
So- you are on to something to try to see how your outfits hit your target look, and which elements of it do that, and what items- tops, bottoms, toppers- are hardest to “ get it” vs easier. I sometimes find I have finally put an “ ideal” outfit together but it seemed so HARD—so partly a sign that some wardrobe items are not closely enough aligned with this in-my-head goal that they are not versatile enough to work easily—like maybe the planets have to align for the right weather and occasion for a particular combination that lets the shirt work, or the pants, or whatever.