Yep it will fit any board and you can run the toe strap either over the top or over the toe.
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It is not waterproof. As far as carrying on a bike that would be your choice. However since it does not have the second sternum strap I do not think it would be ideal for biking.
Nah they would fit perfect. I am a 32-33 waist and I still wear the XL just for extra room and comfort.