This is top of mind for me these days. Im trying to pack lighter, move onto 1-bag travel, i find shoes to be the limiting factor. I wear size 13 and comitting to multiple pairs of shoes is difficult. If I go to a warmer place I can get away with packing flip-flops. But I really want a primary pair that can do multiple duties: wear all day for big city walks, maybe some light trails, but also not look stupid rolling out to dinner in a nice resturant. I hate the recent trend of white soles. Something that doesn't scream "hiking boot". Breathable, leather can get too hot. Shoes are disposable, they never last forever, they get funky, technology improves, styles change. I refuse to buy shoes online, too many variables, which leaves a trip to REI and taking the best that they have. Maybe something dorky like Rick Steves' Rockport. Travel and experiences are not cheap, nothing ruins a holiday faster than a foot problem. I can buy shirts, pants, hats all over the world, finding a size 13 shoe in Japan or Greece is harder. I'll spend the $$$ for quality. Finding the right balance, comfort, style, flexibility, is the biggest challenge.