Here's a blanket statement: if you use eyeliner, I think it should be waterproof.
My friend Janine (who is, incidentally, also a makeup artist) turned me on to the wonders of waterproof liner a couple of years ago, and I've never looked back. (Honestly, it DOES make a difference with the raccoon factor, as I used to forever be wiping errant smudges from my upper and lower lids. Not anymore.)
Benefit does a particularly good job on the waterproofing front—their BADgal waterproof liner is on frequent rotation in my makeup bag—and now the company has come out with Automatic Eyeliner Pencils. As in, no more sharpening AND no more smudges. They draw a really thin line, which is perfect for daytime (you can always build upon it for evening). And the wand is dual-ended, with a sponge tip on the other side for easy blending, if you so choose. Available in three neutral colours—my favourite is Wink O' Ink (a gray-black).
Priced at $26. Available at Holt Renfrew on Bloor St. in Toronto and at Murale, Sephora and Shoppers Drug Mart Beauty Boutiques across Canada.