I own a pair of Double H boots, I believe they're called ranch wellingtons. Nothing fancy, just good quality leather and construction, and they look good. But I can't wear them more than 3 hours or so without my feet really hurting. Good for church or going to a card party, but that's it.
Same with dressy hard leather-type heels and shoes. I wore hard dress shoes last weekend for 8 hours while working a concert. I looked good, but paid the price after I got home.
For everyday wear, I go with New Balance 605's. They're not stylish, but they fit my high instep well and give the heel and toes great support.