Alyssa I vote for short. I've never had tall but I don't want them - the short are so much easier to just throw on, and I think they'd be just as warm because it's really just your feet that need them, not your legs (in my opinion anyway). I resisted the Uggs for SO long but because I take the streetcar to work and I'm often waiting outside at the stop for like 20 mins in the winter, I finally caved and got a pair. They're awesome for the dog park too. I am obsessed with mine now! I'm getting a new pair this year because I've worn my last ones for 2 winters now and they're pretty gross and salt stained. I'll probably just get black again although I really like the gray ones!