I've been getting a lot of questions lately about whether or not to cuff dress trousers. The past 5 years or so have been dominated by suit pants with no cuff providing a clean streamlined look. Now it seems the cuff is making a strong comeback. Truthfully, there is no right or wrong answer to this question. It's really all about preference. Cuffs will never go out of style even if they aren't trending at the moment.
I dictate my decision on the seasons. Living in the Midwest, we are fortunate to experience all four seasons albeit some seem longer than others. This change in weather allows us to have two truly seasonal wardrobes. In the spring and summer, I opt to go cuff-less. My poplin and linen suits, my oxford and chambray pants look and feel better with no cuffs. From Memorial Day until Labor Day you won't see me wearing socks (although I do wear liner socks that can't be seen) and with little to no break on my pants, I like the lighter feeling of not having a cuff. Conversely, once October hits, I pull out my thicker flannel and tweed options. The Midwest winter is often daunting. Chilly October rain storms and falling leaves quickly turn to slushy snow and road salt. Through these months, I opt for a cuffed trouser and a hefty 2" option at that. The fold of the cuff acts as a protectant from the elements. Hopping off the L Train and hoofing it to work in 4 inches of snow and road salt is not easy on any garment but that extra fold of fabric will add a little armor to your pant bottom.
I am not saying my thought process is right. Again, it is all about your taste. You can't go wrong either way.