I think one of the biggest hurdles to get over is understanding the "why". Prior to 2015, I never understood why anyone would pay $250 for a pair of shoes. I should mention that I have a painful, uncommon health condition that affects my feet. If I wear shoes that do not provide good support or are not of good quality, I get severe pain that can majorly interfere with my life. My Brooks running shoes are some of the best running shoes in the world, yet I will reach for my AE shoes over them if I’m walking for a long time. My first AE shoe was the Ashton, when I was forced to wear something nicer for a new job, and I was shocked to find out that they kept my feet pain-free better than any running shoe could. I became a loyal customer when I learned this. Then you throw in the fact that they look good and fit my conservative tastes, it’s a perfect match. I should also mention I've owned Rockports and cheaper dress shoes, and they gave me a lot of foot pain issues. AE has never given me painful feet.