I think the trick to wearing red shoes is to also wear something red near your face, to draw the eye up to your pretty face. Also, I know that red, orange, and yellow go well together as they are next to each other on the color wheel. You can also wear red with other tones of red, lighter or darker, so pinks or burgundy. The complimentary color to red is green. I think you are supposed to have one main color, like white, and then wear the pop of red in your boots and scarf or necklace/earrings. Hope that gives you some ideas. If you are a dramatic type, you could wear all red too! I think blue jeans, a white top, red cardigan and red boots would look really pretty.