Not enough men do this, but you should try rolling up your jeans and khakis for a change. It looks sharp.
Somethings you do have to keep in mind are;
1) Make sure they are not loose fitting pants.
2) 1 or 2 rolls should do the trick.
3) It looks better without socks.
4) If you are feeling ‘iffy’ about it, the last thing you need to eliminate any doubt is confidence. Stylish moves like this always need confidence.