Full offense intended:
There are 3 camps that men fall into when it comes to the length of trousers:
1) Older dudes with no style who mistake a clean, minimal trouser break for "highwaters."
2) Overly-trendy dudes wearing man-capris (actual highwaters).
3) Stylish dudes who actually know how to dress.
And to these men I say:
There's no debate or dialogue to be had here: overly-long trousers that clump at the ankles are sloppy and unslightly. Yeah, I know you think your grandpa was well-dressed, but if you're in constant danger of treading on your own pants then you don't get a seat at the sartorial table until you've found a tailor.
Also, if your grandpa was actually well-dressed and wore longer trousers, they were probably of a fuller cut that enveloped the upper part of his shoe, hence DIDN'T crumple. That's a move; not mad at it.
Look man, sometimes it's cool to roll up your chinos and let them ankles breath during the summer. I get it, and that's totally kosher for casual outings. However, if you're strolling around the financial district on a weekday, it's safe for me to assume you're wearing those ankle-cropped trousers to work. Again, it's fine to show a little sock when walking, but if your hem doesn't reach the back of your shoes when you're standing still, that's a mistake rather than a fashion choice.
Thankfully, this one is easy to fix. Ask your tailor to give your trousers a slanted hem!
Bruce Lee once said that you must master the basics to break free of the basics. A man armed with the skill of style knows what he's doing, and he may choose to go for a fuller vintage-style trouser or an abbreviated ankle-bearing inseam, but he will do so at the right times/places with deliberation and poise.
So yeah, if you think trousers cut to a quarter-break are "highwaters," you're goofing it up bro! If you're walking around the financial district in *actual* highwaters, you are also goofing. And if you're one of the few men who know what they're doing and choose to stray for the norm with deliberate effect -- you just keep on doing you!