Replying to LINE boott bag as a carry-on

So I'm heading to whistler this wenesday and not so sure whether or not I can get away with having my line boot bag make it on as a carry-on with United. Last time I traveled I just slung my boots over my backpack with the powerstraps and had no problem. But my line bag has more room for ski essentials than my other bag. So I wasn't sure whether or not ill make it to the gate with my boot bag in hand. Not about to give my boots to the responsibility of the airline. Yet this bag seems pretty irregularly shaped to make it on. But idk. Anyone else make it on the plane with a boot bag as opposed to a regular backpack?