I have a similar problem. Do you think the clips will work with penny loafers?

 

Go retro look and try x-c ski gaiters. Cordura, goretex, black of course, and velcro back closure. You just step on the strap and slap the velcro ... only takes seconds.

 

hahahaha I just spit water on the desk

 

While I don't like to really say a post is gay, this one is definitely headed in that direction, way more than azzless chaps, fingerless gloves and "why do you care what I wear" threads. But, to add content, in the good ol' days, open primary, used to wear a elastic strap with a snap on the ends to wrap around. My buddy used to get them from the railroad, they used them as a safety feature so your pants didn't get caught in a track switch when you were working. If that happened you were either dead soon or walking the yard in your skivvies.

 

We've got enough players for a complete circle , You're welcome to be the pivot man

 

Bungi cord wrapped around your pant cuff works great. A plus to this is you always have bungi's if you need them.