Isn't this the truth.
My brother's wedding was last weekend and I spent quite a bit of time with my dad as he decided on a shoe to wear with his dark charcoal suit. He ended up going with a dark chili Lexington from the shoebank, as he likes the derby style more than an oxford. I explained to him the rules, just how everyone has been explaining them to @BennJeff but at the end of the day if you are wearing AEs, you are light years ahead of the crowd.
IMO, if you aren't going to go with black or burg, he needs something dark chili or oxblood, which would both go well with dark denim. I personally am OK with wearing most non-black dress shoes with jeans, but I understand why others here shy away from this.
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.
Edited by Lobster33 - 5/2/16 at 2:45pm