I wear cuffed dress pants and a combination of the two (not on the same pants!) for casual pants; never for jeans. Because I am slim, I prefer flat-front rather than pleated pants. I think that cuffed pants have a more finished look. There are many factors that add to or subtract from appearance. I like Warren Buffett's quote: I buy expensive suits. They look cheap on me. And so it goes. Fashion is an enigma. For what it's worth, I shine my shoes, use an umbrella, keep my fingernails clean and trimmed, say thank you as often as possible,occasionally wear a bow tie, and where possible give others the benefit of the doubt.
I think the same is true currently with cuffed trousers. Some industries just tend to be a bit more fashion-forward than others, and, as dumb as it sounds, you might raise an eyebrow or two if you show up with your suit cuffed. Reality bites.
I'll cuff pleated dress trousers I intend to wear with a blazer, but that's it. Flat front dress trousers and any suit pants are never cuffed. Traditionally, cuffs were seen as less formal than going without - which is why one would never cuff tuxedo trousers, for example. Ultimately, though, I just prefer the uncuffed look; the rest is unnecessary rationalization. We dress to please ourselves, right?
Cuffed jeans?!? Heaven forfend! That just looks like hand-me-downs...
I cuff my jeans and taylor my one pair of dress pants. The reason being that 98% of the time I have a retro-esq style, but if im not looking retro-esq that day I don't cuff them. as for the one pair of dress pants...... I don't dress up much.
This is an interesting question. I go either way with cuffs and don't really follow any rules, except one: I wear a lot of western boots with everything, including suits, unless the pants are cuffed. I won't wear western boots with cuffed pants. Beyond that, it's all fair game to me.