I recently got to a point where I realized I'd worn through the soles of two of my most comfortable pairs of sandals. Had I realized how worn they were, I'd have taken them in earlier to be repaired but because they are flats, the signs of wear you get from heeled shoes weren't visible. Future tip, if the soles of my shoes start bending back when they hit a cobblestone or raised paving slab, then the shoes are in dire need of a new sole. I did buy the Madewell sandals I'd liked but they seem to be the kind that will take some breaking in and may not be comfortable until next summer. Similarly, my Mayle clogs may not be the best for my feet.
When I went to England, I was in a tricky situation. Literally the only summer shoes I had that were comfortable and not in tatters were my strappy Surface to Air wedges--which were in dire need of a new heel and sole (thanks to Dad, that was accomplished at a small cobbler in Dersingham) and my green Mayle flats, which got soaked a couple of times and didn't work with all outfits.
As I got a train to Glasgow the night before my conference, mistakenly assuming the first panel was in the morning not at 4.30 p.m., I had time to browse the city and its stores. I came across the following pair of shoes marked down from £65 to £30 in Office. They were amazingly comfortable although I did have to size up and would work with dresses, pants, without tights and with. So I bought them and wore them for the rest of the conference.
Indeed these were so comfortable and answered a couple of needs (pretty mid-heeled shoes, something to wear with cropped pants, something Oxford like that didn't make my feet look huge) that I went back and got another pair in black on my way back. That pair are still at home in the UK, but the other ones are proving invaluable here. They are well made, relatively cheap and have stopped me from buying other, still overpriced pairs of shoes online. After all, the percentage of shoes that we buy that none of us can ever wear because they turn out to be horribly uncomfortable makes shoes the worst item to buy. The rare pair that is comfortable and pretty always turns out to be the pair you wish you'd bought in duplicate. I got two pairs of the Devotte sandals I'm probably going to have to toss and my only regret is that I didn't get four.