Well, I'd pick the pair that would be the most waterproof and have the best traction on packed snow and ice. My experience with early season skiing near the coast is that the snow can be pretty wet during the day which turns into ice in the morning and at night.
I don't know where you are staying in Whistler, but I do know I tend to do a lot of walking around the village in the evening so traction is important and so is comfort after your feet have spent the day in ski boots. I wear my Blundstones boots with my jeans which seems to be pretty much in tune with what everyone else is wearing. Personally, I'd go with the HH because they make a statement without veering into the ski bunny/fashionista realm. But realize that I ski with a rather hardcore group of boarders and ski instructors who get excited about technical wear and fabrics. HH would make the cut but logoed Coach boots would get the rolled eyes. Ski towns are full of cliques so it depends on who you want to hang around.
By the way, I met husband on the slopes of Lake Louise by crashing into him when he turned his back on me during my group ski lesson with him. He actually had a limp for a couple of days but figured he'd better ask me out so he could give me a couple of private lessons to save everyone else on the slope. At least that's his story. Not that I'd recommend it as away to meet someone, but it worked for me...
