When I want to have height and wear heels, which let's face it, is most of the time, but need to give my weary feet a bit of a rest my go-to in the cooler months is a stacked heel bootie. It's comfortable, forgiving on the foot and can be extremely stylish. It's a heel/bootie that will allow you to go the distance on a busy day.
Since I am one of those people who love an extra detail or two, I always try to find something "extra," to help my stacked heel bootie, or any shoe for that matter, stand out. It can be an amazing color (for instance a beautiful cognac suede which I'm still in search of), crazy print, straps and/or buckles, fringe, studs...something that adds edge. For me, a simple leather shoe will never do - however i know there is always a place for an understated leather shoe.
Vince Camuto has some pretty fierce selections, like the Charisa, found here. I've always been a fan of Sole Society and these Kelsita booties in three can't lose colors will definitely add dimension to any look you are creating. I could go on - you get the idea.
I don't think I own any jeans that aren't distressed, so it's easy for me to throw on distressed jeans and a chambray shirt and have a moment I feel cute and comfortable in, that carries me throughout the day.