Suz said it very well, but she left out the most important word, proportion. Being only 5'3", I learned early that hem length is critical for a below the knee length skirt. If I wear high heeled boots, the hem could go a bit longer, but not much. I usually set my hem length while wearing flat or low heeled boots, knowing that heels would also work. My skirt also covers my boot tops. I can't afford a flash of leg at this hem length. I would love to be able to wear the even longer skirts with the flat riding boots a couple of my taller friends can pull off. High heeled boots work better for me. I only wear ankle boots with jeans. When I was thinner, I did wear ankle boots with short skirts and dresses.
I don't think it matters if your outfit looks like retro 70s, as long as it looks good. If it looks good, it's timeless.
Cheers
Julie
