I just started packing for Boston about an hour ago, and I've reached the very crucial "which shoes to bring" portion. I'm trying to limit myself to only 2 pairs, maybe 3 max. One of these being a pair I wear on the plane, which should be of the slip-on variety to make getting through airport security easier. But I feel these shoes should also be wearable during other parts of the trip. And yes, there will be walking. Do I go with the trusty Marcelle clog? Or perhaps the stylish Dansko Jade mary jane? Or maybe the cute grey Clarks mary janes I never wear? Maybe they're too casual? UGH.
This is starting to sound like a word problem with no obvious answer. I think I need some scratch paper...
So yeah. Leaving for Boston tomorrow. Slight panic about the shoes. Will not be able to update until I get back. I plan on taking lots of photos. Of shoes. Or perhaps my bare feet, if I can't decide which ones...

Oh my goodness, I have so often been in the same position! I'm a shoe fanatic too ... which ones did you choose?
Oh, decisions. I'd go with the Jade - easy to slip on and off, stable for urban walking. I've had too many uneven pavement/ungraceful me incidents in my Marcelles, so I no longer consider them the perfect travel shoes.
Personally I opt for Keen mary janes in this situation - too casual, sure, but who cares?!
Docs. Docs go with everything, right?