I seem to get a lot of flack for showing a little ankle everyday when it's warm outside. I cuff most of my pants, whether they're denim or chinos because I like the clean-tailored look... and they make me look a little bit taller (or at least I think so) and they show off my shoes too. Now I am not going Thom Browne short by any means, I'm just eliminating the break, so it's a straight shot from the waist to the ankle. Also a tight roll (works best in a chino) will give the pant a slimmer leg, which I also like very much. Cuffing or rolling the bottom of your pants is definitely a throw-back to another time or preparation for a torrential downpour, but I understand why it was so popular. Speaking of downpours, an elevated cuff has actually saved some of my pants when getting caught in the rain, rather them brushing along a wet sidewalk. Also, I am looking forward to the cold winter months when I can keep the cuff, but show off some fancy socks as opposed to my ankles.
All images courtesy of Lavin Style Tumblr
Except image 2, courtesy of Sartorially Inclined