First off, let me just say that these Kenneth Cole ankle booties are a game-changer. The genuine suede uppers give them a luxe look that's way above their price point, and the almond toe design is sleek without being overly trendy.
The comfort level is unreal for a bootie. The lightly padded footbeds had me walking around the city all day without any complaints - and I'm someone who usually can't wait to kick off my shoes after a few hours. The 1.5" block heel is the perfect sweet spot: enough to give you some lift but still totally walkable.
I wore these with everything from skinny jeans to midi skirts during testing, and they worked beautifully every time. The back zip makes them easy to slip on (though I did notice it can be a bit stiff at first like some reviewers mentioned).
Now for the drawbacks: The black color does transfer slightly onto lighter socks or skin, so maybe opt for nude hose if that bothers you. Also, they do run slightly small - I'd recommend sizing up half if you're between sizes or have wider feet.
After two weeks of near-constant wear, I'm seriously considering getting another pair in tan. They've held up beautifully through rain and daily commuting, with no signs of wear on the soles or stitching.