Step 1: Stylish Shoes
Let's go bottom up. SHOES. As long as you don't have those muzzle-like toe clips on your pedals (which are easily removed), you can bike in any kind of shoe you want.
Most skeptics point to the high heel-- but look at these pictures. It CAN be done. Two things are important to keep in mind while pedaling in stilettos:
1. Use your toes/balls of your feet
2. Maintain that high angle while cycling
You can always turn to the stiletto's close cousin if things aren't going so well between you two: the wedge. Still a high heel, still very much stylish, but with a flat sole that's very easy to ride in.
And consider the sole: Is it made of wood and very slippery? Hold on tight to your handle bars.
And if all else fails, put on a pair of sassy flats and show off your killer heels in your bike basket. You can throw them on once you arrive at your destination.
The only other shoe warnings that come to mind are:
-Make sure those laces are tied.
-I don't care how retro cool they are, one should only be moonwalking in moon-boots.