This is a very subjective question and depends on all kinds of variables like trip activities and such, but I'm still vacillating on whether or not to take mine and wondered if any of you have done the same.
Carry-on bag only so I'll have to wear them on the plane, take them off and back on and such. Probably will not wear them X-mas Eve or X-Mas Day and will be spending at least one entire day baking, so that leaves me with 3 days to wear them, maybe less. My family has planned stuff to do in San Francisco though they're kinda keeping it a secret...
I do like them a lot and they are one of my few options if I want something more polished than a sneaker or sandal. As classic riding boots they go with everything and are comfortable, though constant standing and walking for most of the day makes my feet unhappy. The only other shoes I'll be packing are formal heels and Converse. (If I decide not to bring them I have lace-up calf boots as a compromise.)