I personally have no problem with rolling up my pants, but I usually have an issue of my pants being too tight and unable to roll up past my calf. 

The Extra Leg lets you protect your pants while remaining stylish:

Made by A.P.C. with their revered denim, these pant protectors wrap around your calf to protect your jeans. It looks even cooler when you pair it with a contrasting pair of pants:

Available in raw, black, and white denim. 

[$16, Stroke's Extra Leg]

[Via Valet]

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