I have just one pair and I love them! I live in the cold climate and don't wear in winter as I don't wear socks with them. I got my pair in February for a trip and they work so great for packing. They would not have enough support for me to spend an entire day out sightseeing but they are so nice and small to pack for a few hours to dress up an outfit, usually at night.
I have worn mine to work about 3 days a week from early May until now. They still look like new. The bottom isn't worn. I work 8 hours a day and spend about 3/4 of my day sitting at my desk and the other 1/4 running around.
Yes, they are pricey. However, they appear to last. A few years back I bought cheap ballet flats from Target and I would go through a pair a month! Last summer, I bought Cole Haan's. I went through one pair during the summer and had to replace them. When I bought my Tieks in February the Cole Haan's were in OK shape shown a little wear but I just tossed them. My Cole Haan's were $70 a pair and I would have bought 3 pairs wearing for 2 summers, so $210. My Tieks will go into storage for the winter here in mid October so I hope to get another summer out of them. If I do, they will end up being less than the Cole Haan's.
Also, my feet / shoes don't end up sweaty in these. They are real leather so your feet could actually breathe. My Cole Haan's were patent.
I plan on adding more colors to my wardrobe, I just wanted to start with the most basic pair and see how they worked.